Shirakawa Group
Laboratory of
Green Chemistry
Publications
2024
K. Okuno, S. Sumida, S. Shirakawa*, “Kinetic Resolution of α-Allyl-α-cinnamyl Carboxylic Acids Bearing an All-Carbon Quaternary Stereocenter via Bromolactonization Catalyzed by a Chiral Bifunctional Sulfide”
Asian J. Org. Chem. 2024, 13, e202400405.
[DOI: 10.1002/ajoc.202400405]
https://doi.org/10.1002/ajoc.202400405
S. Sumida, K. Okuno, T. Mori, Y. Furuya, S. Shirakawa*, “Chiral bifunctional sulfide-catalyzed enantioselective bromolactonizations of α- and β-substituted 5-hexenoic acids”
Beilstein J. Org. Chem. 2024, 20, 1794–1799.
[DOI: 10.3762/bjoc.20.158]
https://www.beilstein-journals.org/bjoc/articles/20/158
Thematic Issue: New advances in asymmetric organocatalysis II
T. Mori, S. Sumida, K. Sakata, S. Shirakawa*, “Efficient synthetic methods for α,β-dehydroamino acids as useful and environmentally benign building blocks in biological and materials science”
Org. Biomol. Chem. 2024, 22, 4625–4636.
[DOI: 10.1039/D4OB00507D]
https://doi.org/10.1039/D4OB00507D
K. Okuno, Y. Furuya, S. Shirakawa*, “Organocatalyzed Kinetic Resolution of Racemic Carboxylic Acids”
Eur. J. Org. Chem. 2024, 27, e202300985.
[DOI: 10.1002/ejoc.202300985]
https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202300985
T. Mori, S. Sumida, Y. Furuya, S. Shirakawa*, “Chiral Bifunctional Sulfide-Catalyzed Enantioselective Synthesis of α-Substituted γ-Lactones Bearing a γ-Quaternary Stereocenter”
Synlett 2024, 35, 479–483.
[DOI: 10.1055/a-2161-9513]
https://www.thieme-connect.de/products/ejournals/abstract/10.1055/a-2161-9513
Cluster: 11th Singapore International Chemistry Conference (SICC-11)
2023
R. Nishiyori, T. Mori, S. Shirakawa*, “Catalytic asymmetric CO2 utilization reaction for the enantioselective synthesis of chiral 2-oxazolidinones”
Org. Biomol. Chem. 2023, 21, 4002–4006.
[DOI: 10.1039/D3OB00555K]
https://pubs.rsc.org/en/content/articlelanding/2023/ob/d3ob00555k
K. Okuno, B. Chan, S. Shirakawa*, “Differentiating the Allyl and Propargyl Groups on α-Quaternary Carboxylic Acids via Chiral Bifunctional Sulfide-Catalyzed Kinetic Resolution”
Adv. Synth. Catal. 2023, 365, 1496–1504.
[DOI: 10.1002/adsc.202300145]
https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.202300145
T. Mori, K. Abe, S. Shirakawa*, “Asymmetric Synthesis of α-Spiro-γ-lactones and α-Substituted γ-Lactones via Chiral Bifunctional Sulfide-Catalyzed Bromolactonizations”
J. Org. Chem. 2023, 88, 7830–7838.
[DOI: 10.1021/acs.joc.2c02283]
https://doi.org/10.1021/acs.joc.2c02283
[Special Issue: Modern Enantioselective Catalysis in Organic Chemistry]
R. Nishiyori, T. Mori, K. Okuno, S. Shirakawa*, “Chiral Sulfide and Selenide Catalysts for Asymmetric Halocyclizations and Related Reactions”
Org. Biomol. Chem. 2023, 21, 3263–3275.
[DOI: 10.1039/D3OB00292F]
https://doi.org/10.1039/D3OB00292F
T. Mori, R. Nishiyori, S. Sumida, Y. Furuya, S. Shirakawa*, “Chiral Organocatalysts in Enantioselective CO2 Utilization Reactions”
Eur. J. Org. Chem. 2023, 26, e202300551.
[DOI: 10.1002/ejoc.202300551]
https://doi.org/10.1002/ejoc.202300551
K. Okuno, R. Nishiyori, S. Shirakawa*, “Catalysis by Tertiary Chalcogenonium Salts”
Tetrahedron Chem 2023, 6, 100037.
[DOI: 10.1016/j.tchem.2023.100037]
https://www.tetrahedron-chem.com/article/S2666-951X(23)00003-7/fulltext
S. Shirakawa*, “Bifunctional Onium and Potassium Iodides as Nucleophilic Catalysts for the Solvent-Free Syntheses of Carbonates, Thiocarbonates, and Oxazolidinones from Epoxides”
Chem. Rec. 2023, 23, e202300144.
[DOI: 10.1002/tcr.202300144]
https://onlinelibrary.wiley.com/doi/full/10.1002/tcr.202300144
[Special Issue: Keiji Maruoka's 70th birthday]
B. Chan*, S. Shirakawa, “The prospects of cation transfer to chalcogen nucleophiles”
Can. J. Chem. 2023, 101, 603–614.
[DOI: 10.1139/cjc-2022-0222]
https://cdnsciencepub.com/doi/10.1139/cjc-2022-0222
白川誠司, “CATを愛でる”
化学と工業 2023, 76, 270.
2022
R. Nishiyori, K. Okuno, B. Chan, S. Shirakawa*, “Chiral Bifunctional Selenide Catalysts for Asymmetric Iodolactonizations”
Chem. Pharm. Bull. 2022, 70, 599–604.
[DOI: 10.1248/cpb.c22-00049]
https://doi.org/10.1248/cpb.c22-00049
[Current Topics: Recent Advances in Molecular Space Chemistry]
K. Okuno, R. Nishiyori, K. Abe, T. Mori, S. Shirakawa*, “Efficient Methods for the Synthesis of Chiral 2-Oxazolidinones as Pharmaceutical Building Blocks”
Chirality 2022, 34, 915–924.
[DOI: 10.1002/chir.23452]
https://onlinelibrary.wiley.com/doi/10.1002/chir.23452
[Special Issue: Chirality in Pharmaceutical Research and Development]
K. Okuno, M. Hiraki, B. Chan, S. Shirakawa*, “Non-Enzymatic Kinetic Resolution and Desymmetrization of α-Quaternary Carboxylic Acids via Chiral Bifunctional Sulfide-Catalyzed Bromolactonization”
Bull. Chem. Soc. Jpn. 2022, 95, 52–59.
[DOI: 10.1246/bcsj.20210347]
https://doi.org/10.1246/bcsj.20210347
S. Shirakawa*, “Quaternary Ammonium, Phosphonium, and Tertiary Sulfonium Salts as Hydrogen-Bonding Catalysts”
in Anion-Binding Catalysis (Olga Garcia Mancheno Ed.), Wiley-VCH, Chapter 8, 249–270, 2022.
https://doi.org/10.1002/9783527830664.ch8
白川誠司、奥野研, “オリジナルなキラルスルフィド触媒の開発”
月刊 化学 (化学同人) 2022, 77, 21–25.
https://www.kagakudojin.co.jp/book/b606615.html
2021
M. Hiraki, K. Okuno, R. Nishiyori, A. A. Noser, S. Shirakawa*, “Efficient Asymmetric Syntheses of α-Quaternary Lactones and Esters through Chiral Bifunctional Sulfide-Catalyzed Desymmetrizing Bromolactonization of α,α-Diallyl Carboxylic Acids”
Chem. Commun. 2021, 57, 10907–10910.
[DOI: 110.1039/D1CC03874E]
https://doi.org/10.1039/D1CC03874E
K. Okuno, R. Nishiyori, M. Hiraki, S. Shirakawa*, “Environmentally Benign Synthesis of Cyclic Carbonates from Epoxides and Carbon Dioxide using Binary and Bifunctional Catalysts”
Heterocycles 2021, 103, 94–109.
[DOI: 10.3987/REV-20-SR(K)2] [Review]
https://www.heterocycles.jp/newlibrary/libraries/doi
[Special Issue: Prof. Yasuyuki Kita's 77th Birthday]
R. Nishiyori, M. Okada, J. R. J. Maynard, S. Shirakawa*, “Chiral Bifunctional Sulfide‐Catalyzed Highly Enantioselective Bromolactonizations of 4‐Pentenoic Acids”
Asian J. Org. Chem. 2021, 10, 1444–1448.
[DOI: 10.1002/ajoc.202000644]
https://doi.org/10.1002/ajoc.202000644
K. Okuno, T. Nakamura, S. Shirakawa*, “Asymmetric Catalysis of Chiral Bifunctional Selenides and Selenonium Salts Bearing a Urea Group”
Asian J. Org. Chem. 2021, 10, 655–659.
[DOI: 10.1002/ajoc.202100001]
https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202100001
[Special Issue: Organocatalysis]
白川誠司, “反応空間の精密制御を実現する分子認識型スルフィド触媒の創製”
化学と工業 2021, 74, 90.
2020
R. Nishiyori, K. Okuno, S. Shirakawa*, “Triethylamine Hydroiodide as a Bifunctional Catalyst for the Solvent-Free Synthesis of 2-Oxazolidinones”
Eur. J. Org. Chem. 2020, 4937–4941.
[DOI: 10.1002/ejoc.202000771]
https://doi.org/10.1002/ejoc.202000771
***Highlighted in ChemistryViews : https://www.chemistryviews.org/details/ezine/11254064/Practical_Synthetic_Method_for_2-Oxazolidinones.html
T. Nakamura, K. Okuno, K. Kaneko, M. Yamanaka*, S. Shirakawa*, “Chiral Bifunctional Sulfide-Catalyzed Asymmetric Bromoaminocyclizations”
Org. Biomol. Chem. 2020, 18, 3367–3373.
[DOI: 10.1039/D0OB00459F].
https://pubs.rsc.org/en/content/articlelanding/2020/ob/d0ob00459f/unauth#!divAbstract
R. Nishiyori, J. R. J. Maynard, S. Shirakawa*, “Chiral Bifunctional Selenide Catalysts for Asymmetric Bromolactonization”
Asian J. Org. Chem. 2020, 9, 192–196.
[DOI: 10.1002/ajoc.201900688]
https://onlinelibrary.wiley.com/doi/abs/10.1002/ajoc.201900688
[Special Issue: Celebrating the 100th Annual Meeting of the Chemical Society of Japan (CSJ).]
T. Nakamura, K. Okuno, R. Nishiyori, S. Shirakawa*, “Hydrogen-Bonding Catalysis of Alkyl-Onium Salts”
Chem. Asian J. 2020, 15, 463–472. [DOI: 10.1002/asia.201901652] [Minireview]
https://onlinelibrary.wiley.com/doi/abs/10.1002/asia.201901652
[Special Issue: Celebrating the 100th Annual Meeting of the Chemical Society of Japan (CSJ).]
M. Yamanaka*, A. Mochizuki, T. Nakamura, K. Maruoka, S. Shirakawa*, “Trialkylsulfonium and Tetraalkylammonium Salts as Hydrogen-Bonding Catalysts in an Aza-Diels-Alder Reaction: Experimental and Computational Studies”
Heterocycles 2020, 101, 580–592.
[DOI: 10.3987/COM-19-S(F)48]
https://www.heterocycles.jp/newlibrary/libraries/abst/26423
[Special Issue: Prof. Kaoru Fuji's 80th Birthday]
白川誠司, “温和な条件下でのCO2からの環状カーボネート合成”
脱石油に向けたCO2資源化技術, 第Ⅱ編 第10章, シーエムシー出版, 105–115, 2020.
2019
A. Tsuchihashi, S. Shirakawa*, “Catalyst-Controlled Regio- and Stereoselective Bromolactonization with Chiral Bifunctional Sulfides”
Synlett 2019, 30, 1662–1666. [DOI: 10.1055/s-0037-1610716]
http://dx.doi.org/10.1055%2Fs-0037-1610716
[Published as part of the Cluster Organosulfur and Organoselenium Compounds in Catalysis]
[Selected as Cover]
M. Okada, K. Kaneko, M. Yamanaka, S. Shirakawa*, “BINOL-derived bifunctional sulfide catalysts for asymmetric synthesis of 3,3-disubstituted phthalides via bromolactonization”
Org. Biomol. Chem. 2019, 17, 3747–3751. [DOI: 10.1039/C9OB00417C].
https://pubs.rsc.org/en/content/articlelanding/2019/OB/C9OB00417C#!divAbstract
[Themed collection: Synthetic methodology in OBC].
中村巧、岡田めぐみ、白川誠司*, “環境調和型環状カーボネート合成を志向した触媒反応系の構築”
有機合成化学協会誌 2019, 77, 791–799.
https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/77/8/77_791/_article/-char/ja/
2018
R. Nishiyori, A. Tsuchihashi, A. Mochizuki, K. Kaneko, M. Yamanaka*, S. Shirakawa*, “Design of Chiral Bifunctional Dialkyl Sulfide Catalysts for Regio-, Diastereo-, and Enantioselective Bromolactonization”
Chem. Eur. J. 2018, 24, 16747–16752. [DOI: 10.1002/chem.201803703]. [selected as Hot Paper].
https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201803703
M. Okada, R. Nishiyori, S. Kaneko, K. Igawa, S. Shirakawa*, “KI-Tetraethylene Glycol Complex as an Effective Catalyst for the Synthesis of Cyclic Thiocarbonates from Epoxides and CS2”
Eur. J. Org. Chem. 2018, 2022–2027. [selected as VIP (Very Important Paper) in EJOC].
https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201800284
S. Shirakawa, S. Shimizu, “Inherently Chiral Calix[4]arenes as Supramolecular Catalysts”
in Designed Molecular Space in Material Science and Catalysis, Springer, 51–68, 2018.
https://www.springer.com/jp/book/9789811312557
2017
S. Liu, K. Maruoka, S. Shirakawa*, “Chiral Tertiary Sulfonium Salts as Effective Catalysts for Asymmetric Base-Free Neutral Phase-Transfer Reactions”
Angew. Chem. Int. Ed. 2017, 56, 4819.
S. Shirakawa*, K. Maruoka*, “A New Strategy for Organocatalyzed Asymmetric Synthesis of BINOL Derivatives”
Chem 2017, 2, 329. (Preview)
S. Kaneko, Y. Kumatabara, S. Shimizu, K. Maruoka, S. Shirakawa*, “Hydrogen-Bonding Catalysis of Sulfonium Salts”
Chem. Commun. 2017, 53, 119. [Highlighted in Synfacts 2017, 13, 205.]
S. Kaneko, S. Shirakawa*, “Potassium Iodide-Tetraethylene Glycol Complex as a Practical Catalyst for CO2 Fixation Reactions with Epoxides under Mild Conditions”
ACS Sustainable Chem. Eng. 2017, 5, 2836.
Y. Kumatabara, M. Okada, S. Shirakawa*, “Triethylamine Hydroiodide as a Simple yet Effective Bifunctional Catalyst for CO2 Fixation Reactions with Epoxides under Mild Conditions”
ACS Sustainable Chem. Eng. 2017, 5, 7295. DOI: 10.1021/acssuschemeng.7b01535
白川誠司, “軸不斉ビアリール化合物の新たな合成戦略 ー不斉相間移動反応のさらなる可能性”
月刊化学 2017, 72, 64.
2016
S. Liu, N. Suematsu, K. Maruoka, S. Shirakawa*, “Design of Bifunctional Quaternary Phosphonium Salt Catalysts for CO2 Fixation Reaction with Epoxides under Mild Conditions”
Green Chem. 2016, 18, 4611.
Y. Kumatabara, S. Kaneko, S. Nakata, S. Shirakawa*, K. Maruoka, “Hydrogen-Bonding Catalysis of Tetraalkylammonium Salts in an Aza Diels-Alder Reaction”
Chem. Asian J. 2016, 11, 2126. [Highlighted in Synfacts 2016, 12, 1093.]
S. Shirakawa, X. Wu, S. Liu, K. Maruoka*, “Catalytic Asymmetric Synthesis of Axially Chiral 2-Amino-1,1'-biaryl Compounds by Phase-Transfer-Catalyzed Kinetic Resolution and Desymmetrization”
Tetrahedron 2016, 72, 5163. [Tetrahedron Symposium-in-Print issue on "Methods for controlling axial chirality"]
S. Kaneko, Y. Kumatabara, S. Shirakawa* “A New Generation of Chiral Phase-Transfer Catalysts”
Org. Biomol. Chem. 2016, 14, 5367. [special issue on "New Talent"][Selected as 2016 Hot Articles in OBC]
S. Liu, Y. Kumatabara, S. Shirakawa*, “Chiral Quaternary Phosphonium Salts as Phase-Transfer Catalysts for Environmentally Benign Asymmetric Transformations”
Green Chem. 2016, 18, 331.
S. Shirakawa*, S. Liu, S. Kaneko, “Organocatalyzed Asymmetric Synthesis of Axially, Planar, and Helical Chiral Compounds”
Chem. Asian J. 2016, 11, 330. [special issue on "Catalysis and Transformation of Complex Molecules"]
2015
S. Shirakawa*, S. Liu, S. Kaneko, Y. Kumatabara, A. Fukuda, Y. Omagari, K. Maruoka*, “Tetraalkylammonium Salts as Hydrogen-Bonding Catalysts”
Angew. Chem. Int. Ed. 2015, 54, 15767.
S. Shirakawa, K. Yamamoto, K. Maruoka, “Phase-Transfer-Catalyzed Asymmetric SNAr Reaction of α-Amino Acid Derivatives with Arene Chromium Complexes”
Angew. Chem. Int. Ed. 2015, 54, 838. [Highlighted in Synfacts 2015, 11, 316.]
S. Shirakawa, T. Tokuda, S. B. J. Kan, K. Maruoka, “Phase-Transfer-Catalyzed Asymmetric Desymmetrizations of Cyclopentanones”
Org. Chem. Front. 2015, 2, 336. [Celebrating the 80th Birthday of Professor Ei-ichi Negishi][Selected as 2015 Hot Articles in OCF]
2014
S. Shirakawa, K. Koga, T. Tokuda, K. Yamamoto, K. Maruoka, “Catalytic Asymmetric Synthesis of 3,3’-Diaryloxindoles as Triarylmethanes with a Chiral All-Carbon Quaternary Center: Phase-Transfer-Catalyzed SNAr Reaction”
Angew. Chem. Int. Ed. 2014, 53, 6220. [Highlighted in Synfacts 2014, 10, 869.]
S. Shirakawa, L. Wang, R. He, S. Arimitsu, K. Maruoka, “A Base-Free Neutral Phase-Transfer Reaction System”
Chem. Asian J. 2014, 9, 1586.
S. Shirakawa, K. Yamamoto, T. Tokuda, K. Maruoka, “Phase-Transfer-Catalyzed Asymmetric α-Arylation of α-Amino Acid Derivatives”
Asian J. Org. Chem. 2014, 3, 433. [Highlighted in Synfacts 2014, 10, 532.]
S. Shirakawa, K. Maruoka, “Asymmetric Phase-Transfer Reactions under Base-Free Neutral Conditions”
Tetrahedron Lett. 2014, 55, 3833.
X. Wu, S. Shirakawa, K. Maruoka, “Efficient Asymmetric Synthesis of Spiro-2(3H)-furanones via Phase-Transfer-Catalyzed Alkynylation”
Org. Biomol. Chem. 2014, 12, 5388.
S. Shirakawa, H. Makino, T. Yoshidome, K. Maruoka, “Effect of Brønsted acid co-Catalyst in Asymmetric Conjugate Addition of 3-Aryloxindoles to Maleimide under Base-Free Phase-Transfer Conditions”
Tetrahedron 2014, 70, 7128. [Memorial Issue for Prof. Sandy Mckillop]
白川誠司, “塩基を必要としない中性相間移動反応系の発見と展開”
有機合成化学協会誌 2014, 72, 1374.
2013
S. Shirakawa, X. Wu, K. Maruoka, “Kinetic Resolution of Axially Chiral 2-Amino-1,1’-Biaryls by Phase-Transfer Catalyzed N-Allylation”
Angew. Chem. Int. Ed. 2013, 52, 14200.
S. Shirakawa, K. Maruoka, “Recent Developments in Asymmetric Phase-Transfer Reactions”
Angew. Chem. Int. Ed. 2013, 52, 4312.
S. Shirakawa, A. Kasai, T. Tokuda, K. Maruoka, “Efficient Approach for the Design of Effective Chiral Quaternary Phosphonium Salts in Asymmetric Conjugate Additions”
Chem. Sci. 2013, 4, 2248.
S. Shirakawa, T. Tokuda, A. Kasai, K. Maruoka, “Design of Chiral Bifunctional Quaternary Phosphonium Bromide Catalysts Possessing an Amide Moiety”
Org. Lett. 2013, 15, 3350.
Y. Liu, S. Shirakawa, K. Maruoka, “Phase-Transfer-Catalyzed Asymmetric Conjugate Cyanation of Alkylidenemalonates with KCN in the Presence of a Brønsted Acid Additive”
Org. Lett. 2013, 15, 1230. [Highlighted in Synfacts 2013, 9, 553.]
S. Shirakawa, A. Usui, S. B. J. Kan, K. Maruoka, “Chiral Organotin Hydride-Catalyzed Enantioselective Radical Cyclization of Aldehydes”
Asian J. Org. Chem. 2013, 2, 916. [Highlighted in ChemistryViews 2013, 11.13.]
K. Liu, X. Wu, S. B. J. Kan, S. Shirakawa, K. Maruoka, “Phase-Transfer-Catalyzed Asymmetric Synthesis of Axially Chiral Anilides”
Chem. Asian J. 2013, 8, 3214.
S. Shimizu, A. Usui, M. Sugai, Y. Suematsu, S. Shirakawa, H. Ichikawa, “Hexameric Capsule of a Resorcinarene Bearing Fluorous Feet as a Self-Assembled Nanoreactor: A Diels–Alder Reaction in a Fluorous Biphasic System”
Eur. J. Org. Chem. 2013, 4734.
S. Shirakawa, K. Yamamoto, K. Liu, K. Maruoka, “Enantioselective Alkylation of 2-[(4-Chlorobenzyliden)Amino] Propanoic Acid tert-Butyl Ester: Synthesis of (R)-2-Amino-2-Methyl-3-Phenylpropanoic Acid tert-Butyl Ester”
Org. Synth. 2013, 90, 121.
S. Shirakawa, K. Yamamoto, K. Liu, K. Maruoka, “Enantioselective Alkylation of N-(Diphenylmethylene)glycinate tert-Butyl Ester: Synthesis of (R)-2-(Benzhydrylidenamino)-3- Phenylpropanoic Acid tert-Butyl Ester”
Org. Synth. 2013, 90, 112.
S. Shirakawa, K. Maruoka, “Chiral Onium Salts”
in Comprehensive Enantioselective Organocatalysis, Wiley, 365–379, 2013.
白川誠司, “中性条件下での相間移動反応”
化学と工業 2013, 66, 735.
2012
S. Shirakawa, K. Liu, K. Maruoka, “Catalytic Asymmetric Synthesis of Axially Chiral o-Iodoanilides by Phase-Transfer Catalyzed Alkylations”
J. Am. Chem. Soc. 2012, 134, 916. [Highlighted in Synfacts 2012, 8, 333.]
S. Shirakawa, L. Wang, A. Kasai, K. Maruoka, “New Neutral Reaction System with Crown Ether–KCl Complexes in Aqueous Solution”
Chem. Eur. J. 2012, 18, 8588.
S. Shirakawa, K. Ota, S. J. Terao, K. Maruoka, “The Direct Catalytic Asymmetric Aldol Reaction of α-Substituted Nitroacetates with Aqueous Formaldehyde under Base-Free Neutral Phase-Transfer Conditions”
Org. Biomol. Chem. 2012, 10, 5753. [OBC 10th anniversary issue]
S. Shirakawa, Y. Liu, A. Usui, K. Maruoka, “Efficient Asymmetric Synthesis of a Bicyclic Amino Acid as a Core Structure of Telaprevir”
ChemCatChem 2012, 4, 980. [Organocatalysis special issue]
Y. Kubota, S. Shirakawa, T. Inoue, K. Maruoka, “New Chiral Phase-Transfer Catalysts Possessing a 6,6’-Bridged Ring on the Biphenyl Unit: Application to the Synthesis of α,α-Dialkyl-α-amino Acids”
Tetrahedron Lett. 2012, 53, 3739.
Y. Liu, A. Usui, S. Shirakawa, K. Maruoka, “Catalytic Asymmetric Synthesis of 3-Substituted Proline Derivatives by Using Phase-Transfer-Catalyzed Conjugate Addition”
Asian J. Org. Chem. 2012, 1, 180.
S. Shirakawa, S. A. Moteki, K. Maruoka, “Asymmetric Phase-Transfer Catalysis”
in Modern Tools for the Synthesis of Complex Bioactive Molecules, Wiley, 213–242, 2012.
S. Shirakawa, K. Maruoka, “Phase-Transfer Catalysis: Non-Natural-Product-Derived PTC”
in Science of Synthesis: Asymmetric Organocatalysis 2, Thieme, 551–599, 2012.
S. Shirakawa, K. Maruoka, “Asymmetric α-Functionalization of Carbonyl Compounds and Alkylation of Enolates”
in Science of Synthesis: Water in Organic Synthesis, Thieme, 601–615, 2012.
S. Shirakawa, K. Maruoka, “Comment 1 for the Proline-Catalyzed Mannich Reaction and the Advent of Enamine Catalysis”
in Organic Chemistry –Breakthrough and Perspective, Wiley-VCH, 375–377, 2012.
白川誠司, 丸岡啓二, “中性条件下で進む不斉相間移動反応 –生体内反応系により近い反応系を実現!!–”
月刊化学 2012, 67, 18.
2011
L. Wang, S. Shirakawa, K. Maruoka, “Asymmetric Neutral Amination of Nitroolefins Catalyzed by Chiral Bifunctional Ammonium Salts in Water-Rich Biphasic Solvent”
Angew. Chem. Int. Ed. 2011, 50, 5327. [Highlighted in Synfacts 2011, 7, 791.]
S. Shirakawa, S. J. Terao, R. He, K. Maruoka, “Diastereo- and Enantioselective Conjugate Addition of α-Substituted Nitroacetates to Maleimides under Base-Free Neutral Phase-Transfer Conditions”
Chem. Commun. 2011, 47, 10557.
S. Shirakawa, K. Liu, H. Ito, K. Maruoka, “Catalytic Asymmetric Synthesis of 1,1-Disubstituted Tetrahydro-β-carbolines by Phase-Transfer Catalyzed Alkylations”
Chem. Commun. 2011, 47, 1515. [Highlighted in Synfacts 2011, 2, 210.]
S. Shirakawa, K. Liu, H. Ito, K. Maruoka, “Phase-Transfer Catalyzed Asymmetric Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines”
Adv. Synth. Catal. 2011, 353, 2614.
S. Shirakawa, K. Maruoka, “tert-Butyl N-(Diphenylmethylene)glycinate”
in E-EROS Encyclopedia of Reagents for Organic Synthesis, 10.1002/047084289X.rn01269, 2011.
S. A. Moteki, S. Shirakawa, K. Maruoka, “(1R)-3,3′-Bis(2,4,6-trimethylphenyl) [1,1′-binaphthalene] -2,2′-dicarboxylic Acid”
in E-EROS Encyclopedia of Reagents for Organic Synthesis, 10.1002/047084289X.rn01270, 2011.
2010
X. Wang, Q. Lan, S. Shirakawa, K. Maruoka, “Chiral Bifunctional Phase Transfer Catalysts for Asymmetric Fluorination of β-Keto Esters”
Chem. Commun. 2010, 46, 321.
Q. Lan, X. Wang, S. Shirakawa, K. Maruoka, “Phase-Transfer Catalyzed Asymmetric Conjugate Additions of β-Ketoesters to Acetylenic Ketones”
Org. Process Res. Dev. 2010, 14, 684. [Phase Transfer Catalysis special issue]
S. Shirakawa, S. Shimizu, “Improved Design of Inherently Chiral Calix[4]arenes as Organocatalysts”
New J. Chem. 2010, 34, 1217.
S. Shirakawa, K. Maruoka, “Asymmetric Phase-Transfer and Ion Pair Catalysis”
in Catalytic Asymmetric Synthesis, 3rd ed., John Wiley, 95–117, 2010.
丸岡啓二, 白川誠司, “グリシン誘導体の直截的不斉アルドール反応”
使える!有機合成反応241実践ガイド, 化学同人, 252–253, 2010.
丸岡啓二, 白川誠司, “オキシインドール誘導体の不斉共役付加反応”
使える!有機合成反応241実践ガイド, 化学同人, 278–279, 2010.
2009
R. He, S. Shirakawa, K. Maruoka, “Enantioselective Base-Free Phase-Transfer Reaction in Water-Rich Solvent”
J. Am. Chem. Soc. 2009, 131, 16620.
S. Shirakawa, T. Kimura, S. Murata, S. Shimizu, “Synthesis and Resolution of a Multifunctional Inherently Chiral Calix[4]arene with an ABCD Substitution Pattern at the Wide Rim: the Effect of a Multifunctional Structure in the Organocatalyst on Enantioselectivity in Asymmetric Reactions”
J. Org. Chem. 2009, 74, 1288.
S. Shirakawa, S. Shimizu, “Synthesis of an Inherently Chiral Calix[4]arene Amino Acid and Its Derivatives: Their Application to Asymmetric Reactions as Organocatalysts”
Eur. J. Org. Chem. 2009, 1916.
白川誠司, 丸岡啓二, “デザイン型キラル相間移動触媒を用いる実用的不斉合成”
進化を続ける有機触媒, 化学同人, 23–32, 2009.
2008
S. Shirakawa, A. Moriyama, S. Shimizu, “Synthesis, Optical Resolution, and Enantiomeric Recognition Ability of Novel Inherently Chiral Calix[4]arenes: Trial Application to Asymmetric Reactions as Organocatalysts”
Eur. J. Org. Chem. 2008, 5957.
S. Shirakawa, Y. Tanaka, T. Kobari, S. Shimizu, “Synthesis and Optical Resolution of an Inherently Chiral Calix[4]arene Amino Acid”
New J. Chem. 2008, 32, 1835.
S. Shirakawa, S. Shimizu, “Dehydrative Amination of Alcohols in Water Using a Water-Soluble Calix[4]resorcinarene Sulfonic Acid”
Synlett 2008, 1539.
M. Kitamura, S. Shirakawa, Y. Arimura, X. Wang, K. Maruoka, “Combinatorial Design of Simplified High Performance Chiral Phase-Transfer Catalysts for Practical Asymmetric Synthesis of α-Alkyl- and α,α-Dialkyl-α-Amino Acids”
Chem. Asian J. 2008, 3, 1702.
M. Kitamura, Y. Arimura, S. Shirakawa, K. Maruoka, “Combinatorial Approach for the Design of New, Simplified Chiral Phase-Transfer Catalysts with High Catalytic Performance for Practical Asymmetric Synthesis of α-Alkyl-α-Amino Acids”
Tetrahedron Lett. 2008, 49, 2026.
T. Kano, A. Yamamoto, H. Mii, J. Takai, S. Shirakawa, K. Maruoka, “Direct Asymmetric Aminoxylation Reaction Catalyzed by Axially Chiral Amino Acids”
Chem. Lett. 2008, 37, 250.
S. Shirakawa, T. Ooi, K. Maruoka, “Chiral Quaternary Ammonium Fluorides for Asymmetric Synthesis”
in Asymmetric Phase Transfer Catalysis, Wiley-VCH, 189–206, 2008.
2007
S. Shirakawa, S. Kobayashi, “Surfactant-Type Brønsted Acid Catalyzed Dehydrative Nucleophilic Substitutions of Alcohols in Water”
Org. Lett. 2007, 9, 311.
S. Shirakawa, A. Moriyama, S. Shimizu, “Design of a Novel Inherently Chiral Calix[4]arene for Chiral Molecular Recognition”
Org. Lett. 2007, 9, 3117.
S. Shirakawa, S. Shimizu, “Hydrogen-Bond-Promoted C–C Bond Forming Reaction: Catalyst-Free Michael Addition Reactions in Ethanol”
Synlett 2007, 3160.
S. Shirakawa, M. Ueda, Y. Tanaka, T. Hashimoto, K. Maruoka, “Design of Binaphthyl-Modified Symmetrical Chiral Phase-Transfer Catalysts: Substituent Effect of 4,4’,6,6’-Positions of Binaphthyl Rings in the Asymmetric Alkylation of Glycine Derivative”
Chem. Asian J. 2007, 2, 1276.
2006
S. Shirakawa, S. Kobayashi, “Carboxylic Acid Catalyzed Three-Component Aza-Friedel–Crafts Reactions in Water for the Synthesis of 3-Substituted Indoles”
Org. Lett. 2006, 8, 4939.
S. Shirakawa, S. Kobayashi, “Ag(I)-Catalyzed Michael Additions of β-Ketoesters to Nitroalkenes in Water: Remarkable Effect of Water as a Reaction Medium on Reaction Rates”
Synlett 2006, 1410. [Highlighted in Synfacts 2006, 801.]
2005
S. Shirakawa, K. Yamamoto, M. Kitamura, T. Ooi, K. Maruoka, “Dramatic Rate Enhancement of Asymmetric Phase-Transfer-Catalyzed Alkylations”
Angew. Chem. Int. Ed. 2005, 44, 625.
M. Kitamura, S. Shirakawa, K. Maruoka, “Powerful Chiral Phase-Transfer Catalysts for the Asymmetric Synthesis of α-Alkyl- and α,α-Dialkyl-α-Amino Acids”
Angew. Chem. Int. Ed. 2005, 44, 1549.
S. Shirakawa, R. Berger, J. L. Leighton, “Enantioselective Friedel–Crafts Alkylations with Benzoylhydrazones Promoted by a Simple Strained Silacycle Reagent”
J. Am. Chem. Soc. 2005, 127, 2858. [Highlighted in Synfacts 2005, 48.]
S. Shirakawa, P. J. Lombardi, J. L. Leighton, “A Simple and General Chiral Silicon Lewis Acid for Asymmetric Synthesis: Highly Enantioselective [3+2] Acylhydrazone-Enol Ether Cycloadditions”
J. Am. Chem. Soc. 2005, 127, 9974.
2004
S. Shirakawa, Y. Tanaka, K. Maruoka, “Development of a Recyclable Fluorous Chiral Phase-Transfer Catalyst: Application to the Catalytic Asymmetric Synthesis of α-Amino Acids”
Org. Lett. 2004, 6, 1429.
T. Kano, S. Konishi, S. Shirakawa, K. Maruoka, “Design of New Polyamine-Based Chiral Phase-Transfer Catalysts for the Enantioselective Synthesis of Phenylalanine”
Tetrahedron: Asymmetry 2004, 15, 1243.
2003
S. Shirakawa, J. Takai, K. Sasaki, T. Miura, K. Maruoka, “Bowl-Shaped [Tris(2,6-diphenylbenzyl)siloxy]dimethylaluminum Catalyst for Effecting Tishchenko Reaction”
Heterocycles 2003, 59, 57.
S. Shirakawa, K. Maruoka, “Synthetic Utility of Bowl-Shaped Tris(2,6-diphenylbenzyl)silyl Glyoxylate as a Stable Glyoxylate: Application to Highly Diastereoselective Aldol Reactions”
Tetrahedron Lett. 2003, 44, 281.
2002
S. Shimizu, T. Suzuki, S. Shirakawa, Y. Sasaki, C. Hirai, “Water-Soluble Calixarenes as New Inverse Phase-Transfer Catalysts. Their Scope in Aqueous Biphasic Alkylations and Mechanistic Implications”
Adv. Synth. Catal. 2002, 344, 370.
S. Shirakawa, N. Komatsu, A. Iwasaki, K. Maruoka, “Unusually Stable Silyl Ketones with Bowl-Shaped Tris(2,6-diphenylbenzyl)silyl Group for Various Nucleophilic Attacks and α-Deprotonation”
Synlett 2002, 577.
K. Sasaki, N. Komatsu, S. Shirakawa, K. Maruoka, “Chemoselective Reduction of Saturated Aldehydes and Ketones over Unsaturated Carbonyls with Bowl-Shaped Tris(2,6-diphenylbenzyl)tin Hydride”
Synlett 2002, 575.
S. Shirakawa, K. Maruoka, “A Highly Chemoselective Mukaiyama Aldol Reaction of Saturated Aldehyde over Unsaturated Aldehyde with Enol Tris(2,6-diphenylbenzyl)silyl Ether”
Tetrahedron Lett. 2002, 43, 1469.
2001
M. Naiki, S. Shirakawa, K. Kon-i, Y. Kondo, K. Maruoka, “Tris(2,6-diphenylbenzyl)amine (TDA) and Tris(2,6-diphenylbenzyl)phosphine (TDP) with Unique Bowl-Shaped Structures: Synthetic Application of Functionalized TDA to Chemoselective Silylation of Benzylic Alcohols”
Tetrahedron Lett. 2001, 42, 5467.
S. Shimizu, S. Shirakawa, T. Suzuki, Y. Sasaki, “Water-soluble Calixarenes as New Inverse Phase-Transfer Catalysts. Their Application to Aldol-Type Condensation and Michael Addition Reactions in Water”
Tetrahedron 2001, 57, 6169.
S. Shirakawa, S. Shimizu, Y. Sasaki, “Rhodium-Catalyzed Biphasic Hydroformylation of 4-Octene Using Water-Soluble Calix[4]arene-Phosphine Ligands”
New J. Chem. 2001, 25, 777.
2000
S. Shimizu, S. Shirakawa, Y. Sasaki, C. Hirai, “Novel Water-Soluble Calix[4]arene Ligands with Phosphane-Containing Groups for Dual Functional Metal-Complex Catalysts: The Biphasic Hydroformylation of Wate-Insoluble Olefins”
Angew. Chem. Int. Ed. 2000, 39, 1256.
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