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

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