Enantioselective Assembly of Spirolactones through NHC-Catalyzed Remote γ-Carbon Addition of Enals with Isatins

被引：20

作者：

Rong, Xianfeng ^{[1
,2
]}

Yao, Hong ^{[2
]}

Xia, Wenjing ^{[2
]}

Du, Yonglei ^{[1
,2
]}

Zhou, Yu ^{[2
]}

Liu, Hong ^{[2
]}

机构：

[1] Univ Sci & Technol China, Nano Sci & Technol Inst, 166 Ren Ai Rd, Suzhou 215123, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China

来源：

ACS COMBINATORIAL SCIENCE | 2016年 / 18卷 / 05期

基金：

中国国家自然科学基金;

关键词：

isatins; gamma-carbon; spirolactones; N-HETEROCYCLIC CARBENE; SPIROCYCLIC OXINDOLE-DIHYDROPYRANONES; COOPERATIVE CATALYSIS; CONJUGATE UMPOLUNG; SPIRO COMPOUNDS; ALPHA; BETA-UNSATURATED ALDEHYDES; QUATERNARY STEREOCENTERS; ACID; ACTIVATION; ESTERS;

D O I：

10.1021/acscombsci.5b00197

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A chiral N-heterocyclic carbene (NHC)-catalyzed formal [4+2] annulation of beta-methyl substituted enals with isatins was developed to construct six-membered spirolactones bearing highly congested quaternary carbon stereocentersin good yields and high enantioselectivities. The strategy realized a challenging remote gamma-carbon addition of enals and chiral control of beta-methyl substituted enals in the presence of the NHC catalyst only.

引用

页码：220 / 224

页数：5

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