Transition-Metal-Free Synthesis of Tertiary Aminocyclopropanes

被引：30
|
作者：
Cyr, Patrick [1 ]
Cote-Raiche, Alexandre [1 ]
Bronner, Sarah M. [1 ]
机构：
[1] Genentech Inc, Discovery Chem, 1 DNA Way, San Francisco, CA 94080 USA
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 24期
关键词：
ALPHA-AMINO-ACIDS; GENERATED IN-SITU; STEREOSELECTIVE-SYNTHESIS; 1-AMINOCYCLOPROPANECARBOXYLIC ACID; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC CYCLOPROPANATION; ENANTIOSELECTIVE SYNTHESIS; AMIDES; CYCLOPROPYLAMINE; ALKENES;
D O I：
10.1021/acs.orglett.6b03345
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A transition-metal-free methodology for the construction of pharmaceutically relevant tertiary aminocyclopropanes is reported. Hydrazonamides, safe and stable carbene precursors, undergo smooth cyclopropanation with vinyl arenes in the presence of a base. The reaction proceeds with stereoselectivity to favor the Z isomer and provides facile access to a variety of substitution patterns through variation of the coupling partners.
引用
收藏
页码：6448 / 6451
页数：4
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