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

页码：5412 / 5415

页数：4

共 54 条

[51] N-Heterocyclic Carbene-Catalyzed Homoenolate Additions with N-Aryl Ketimines as Electrophiles: Efficient Synthesis of Spirocyclic γ-Lactam Oxindoles
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[53] Late-Stage Diversification of Chiral N-Heterocyclic-Carbene Precatalysts for Enantioselective Homoenolate Additions
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[J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (02) : 614 - 620
[54] Highly efficient Au(I)-catalyzed intramolecular addition of β-ketoamide to unactivated alkenes
Zhou, Cong-Ying
Che, Chi-Ming
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) : 5828 - +

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