Cinchona Alkaloid Catalyzed Regio- and Enantioselective Allylic Amination of Morita-Baylis-Hillman Carbonates with Isatins

被引：32

作者：

Zhao, Mei-Xin ^{[1
,2
,3
]}

Chen, Ming-Xiao ^{[1
,2
]}

Tang, Wen-Hao ^{[1
,2
]}

Wei, Deng-Ke ^{[1
,2
]}

Dai, Tong-Lei ^{[1
,2
]}

Shi, Min ^{[1
,2
,4
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China

[4] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 19期

基金：

中国国家自然科学基金;

关键词：

Organocatalysis; Amination; Alkaloids; Allylic compounds; Isatins; Carbonates; N-SULFONATED IMINES; METHYL VINYL KETONE; KINETIC RESOLUTION; ACTIVATED OLEFINS; HILIMAN REACTION; ALKYLATION; SUBSTITUTION; ADDUCTS; TRIFLUOROMETHYLATION; ORGANOCATALYSTS;

D O I：

10.1002/ejoc.201200376

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient enantioselective allylic amination of MoritaBaylisHillman (MBH) carbonates derived from methyl acrylate and aromatic aldehydes with isatins has been realized in the presence of commercially available cinchona alkaloids. The allylic amination products were obtained in moderate-to-good yields (4674?%) with moderate-to-good enantioselectivities (up to 89?% ee) under mild conditions. The synthetic utility of the amination products has been well demonstrated by the facile synthesis of methyl (3R,4R)-10-oxo-4-phenyl-2,3,4,10-tetrahydropyrimido[1,2-a]indole-3-carboxylate.

引用

页码：3598 / 3606

页数：9

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