Issue 2, 2018
From the journal:

Organic & Biomolecular Chemistry

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

Vladimir Maslivetc,a   Colby Barrett,a   Nicolai A. Aksenov,b   Marina Rubinaac  and  Michael Rubin ORCID logo *ab  

* Corresponding authors

a Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr., Lawrence, KS 66045-7582, USA
E-mail: mrubin@ku.edu
Tel: +1-785-864-5071

b Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russian Federation

c Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya st., Moscow 117198, Russian Federation

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/C7OB02068F
Article type
Paper
Submitted
18 Aug 2017
Accepted
08 Dec 2017
First published
08 Dec 2017
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2018,16, 285-294

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

V. Maslivetc, C. Barrett, N. A. Aksenov, M. Rubina and M. Rubin, Org. Biomol. Chem., 2018, 16, 285 DOI: 10.1039/C7OB02068F

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