Highly Enantioselective Addition of Enals to Isatin-Derived Ketimines Catalyzed by N-Heterocyclic Carbenes: Synthesis of Spirocyclic γ-Lactams

被引：173
作者：
Lv, Hui [1 ]
Tiwari, Bhoopendra [1 ]
Mo, Junming [1 ]
Xing, Chong [1 ]
Chi, Yonggui Robin [1 ]
机构：
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 21期
基金：
新加坡国家研究基金会;
关键词：
STEREOSELECTIVE-SYNTHESIS; COOPERATIVE CATALYSIS; HOMOENOLATE ADDITIONS; EFFICIENT SYNTHESIS; RING EXPANSION; BETA-LACTAM; ROUTE; ACIDS; ELECTROPHILES;
D O I：
10.1021/ol302475g
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 annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-gamma-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).
引用
收藏
页码：5412 / 5415
页数：4
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