Kinetic Resolution of Tertiary Alcohols by Chiral DMAP Derivatives: Enantioselective Access to 3-Hydroxy-3-substituted 2-Oxindoles

被引：21

作者：

Mandai, Hiroki ^{[2
]}

Shiomoto, Ryuhei ^{[1
]}

Fujii, Kazuki ^{[1
]}

Mitsudo, Koichi ^{[1
]}

Suga, Seiji ^{[1
]}

机构：

[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Appl Chem, Okayama 7008530, Japan

[2] Gifu Univ Med Sci, Fac Pharm, Dept Pharm, Gifu 5090293, Japan

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 04期

关键词：

D O I：

10.1021/acs.orglett.0c03956

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed an efficient acylative kinetic resolution of 3-hydroxy-3-substituted 2-oxindoles by a chiral DMAP derivative having a 1,1'- binaphthyl with two tert-alcohols units. A wide range of 3-hydroxy-3-substituted oxindoles having various functional groups were efficiently resolved (14 examples, up to s = 60) in the presence of 1 mol % of catalyst within 3-9 h. Multigram-scale reactions (10 g) also proceeded with a high s-factor (s = 43) within 5 h.

引用

页码：1169 / 1174

页数：6

共 50 条

[1] Kinetic Resolution of Tertiary Alcohols: Highly Enantioselective Access to 3-Hydroxy-3-Substituted Oxindoles
Lu, Shenci
Poh, Si Bei
Siau, Woon-Yew
Zhao, Yu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (06) : 1731 - 1734
[2] ArPNO-catalyzed acylative kinetic resolution of tertiary alcohols: access to 3-hydroxy-3-substituted oxindoles
Yang, Min
Gao, Yu-Lin
Xie, Ming-Sheng
Guo, Hai-Ming
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (32) : 6351 - 6355
[3] Kinetic Resolution of 3-Hydroxy-3-Substituted Oxindoles through NHC-Catalyzed Oxidative Esterification
Lu, Shenci
Poh, Si Bei
Siau, Woon-Yew
Zhao, Yu
SYNLETT, 2013, 24 (10) : 1165 - 1169
[4] Highly Enantioselective Synthesis of 3-Amino-2-oxindole Derivatives: Catalytic Asymmetric α-Amination of 3-Substituted 2-Oxindoles with a Chiral Scandium Complex
Yang, Zhigang
Wang, Zhen
Bai, Sha
Shen, Ke
Chen, Donghui
Liu, Xiaohua
Lin, Lili
Feng, Xiaoming
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (22) : 6632 - 6637
[5] Nonenzymatic dynamic kinetic resolution of alcohols catalyzed by planar-chiral DMAP derivatives
Lee, Sarah Y.
Murphy, Jaclyn M.
Fu, Gregory C.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[6] KINETIC RESOLUTION OF SECONDARY ALCOHOLS BY CHIRAL DMAP DERIVATIVES PREPARED BY THE UGI MULTICOMPONENT REACTION
Mandai, Hiroki
Irie, Shunsuke
Akehi, Masaru
Yuri, Kazunobu
Yoden, Masaaki
Mitsudo, Koichi
Suga, Seiji
HETEROCYCLES, 2013, 87 (02) : 329 - 340
[7] Theoretical Prediction of Selectivity in Kinetic Resolution of Secondary Alcohols Catalyzed by Chiral DMAP Derivatives
Larionov, Evgeny
Mahesh, Mohan
Spivey, Alan C.
Wei, Yin
Zipse, Hendrik
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) : 9390 - 9399
[8] Preparation of chiral DMAP derivatives and investigation on their enantioselective catalytic activity in benzazetidine synthesis and kinetic resolutions of alcohols
Placidi, Simone
Majnoni D'Intignano, Tea
Salvio, Riccardo
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2022, 59 (09) : 1626 - 1634
[9] Catalytic enantioselective synthesis of 3-hydroxy-2-oxindoles and 3-spirocyclic-2-oxindoles
Hanhan, Nadine V.
Ball-Jones, Nicolas R.
Franz, Annaliese K.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[10] Aldol Insights: The Route to Chiral Synthesis of 3-Substituted 3-Hydroxy-2-Oxindoles
Kaur, Jasneet
Kaur, Sukhmeet
Kaur, Kirandeep
CHEMISTRYSELECT, 2024, 9 (10):

← 1 2 3 4 5 →