Asymmetric Synthesis of C2-Quaternary Indolin-3-ones Enabled by N-Heterocyclic Carbene Catalysis

被引：29
|
作者：
Fang, Shuaishuai [1 ]
Jin, Shiyi [1 ]
Ma, Rui [1 ]
Lu, Tao [1 ]
Du, Ding [1 ]
机构：
[1] China Pharmaceut Univ, Sch Sci, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 13期
基金：
中国国家自然科学基金;
关键词：
CYCLIC C-ACYLIMINES; DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; 4+2 CYCLIZATION; ACTIVATION; KETIMINES; ISATINS; ESTERS; ROUTE; ALPHA;
D O I：
10.1021/acs.orglett.9b01823
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An N-heterocyclic carbene (NHC)-catalyzed formal [4 + 2] annulation of 2-aryl-3H-indol-3-ones with alpha,beta-unsaturated carboxylic acids bearing gamma-H was developed via an in situ activation strategy. The reaction involves the gamma-addition of vinyl enolates to the unique cyclic ketimines to afford chiral tricyclic indolin-3-ones with a quaternary carbon center at 2-position. This protocol provides a rapid and enantioselective pathway to access a novel class of structurally important C2-quaternary indolin-3-ones that might be useful for drug discovery.
引用
收藏
页码：5211 / 5214
页数：4
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