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

页码：285 / 294

页数：10

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