Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes

被引：8
|
作者：
Maslivetc, Vladimir [1 ]
Barrett, Colby [1 ]
Aksenov, Nicolai A. [2 ]
Rubina, Marina [1 ,3 ]
Rubin, Michael [1 ,2 ]
机构：
[1] Univ Kansas, Dept Chem, 1251 Wescoe Hall Dr, Lawrence, KS 66045 USA
[2] North Caucasus Fed Univ, Dept Chem, 1a Pushkin St, Stavropol 355009, Russia
[3] Peoples Friendship Univ Russia, 6 Miklukho Maklaya St, Moscow 117198, Russia
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 02期
基金：
美国国家科学基金会; 俄罗斯基础研究基金会;
关键词：
LITHIUM DERIVATIVES; EN-ROUTE; ENANTIOSELECTIVE DESYMMETRIZATION; 1,2-AND 1,3-DIAMINOALKANES; CATALYZED CARBOZINCATION; CYCLIC ETHERS; EASY ACCESS; SUBSTITUTION; BROMOCYCLOPROPANES; CYCLIZATION;
D O I：
10.1039/c7ob02068f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unusual reaction is described, involving a formal intramolecular nucleophilic substitution of bromocyclopropanes with nitrogen ylides generated in situ from N-benzyl carboxamides. It is shown that this reaction involves cyclopropene intermediates and allows for the facile and expeditious preparation of 3-azabicyclo[3.1.0]hexan-2-one scaffolds.
引用
收藏
页码：285 / 294
页数：10
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