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
收藏
页码：220 / 224
页数：5
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