Enantioselective Synthesis of Aza-β-lactams via NHC-Catalyzed [2+2] Cycloaddition of Ketenes with Diazenedicarboxylates

被引：67

作者：

Huang, Xue-Liang ^{[1
]}

Chen, Xiang-Yu ^{[1
]}

Ye, Song ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 19期

基金：

美国国家科学基金会;

关键词：

ASYMMETRIC ALPHA-AMINATION; CYANOACETATES; SALTS;

D O I：

10.1021/jo901656q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Heterocyclic carbenes were round to be efficient catalysts for the formal [2 + 2] cycloaddition of aryl(alkyl)ketenes and diazenedicarboxylates to give the corresponding aza-beta-lactams in good yields with up to 91% ee. The N-substituent (carboxylate vs benzoyl) of diazenes played an Important role to control the reaction modes (formal [2 + 2] vs [4 + 21 cycloaddtions).

引用

收藏

页码：7585 / 7587

页数：3

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