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

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.

SUBMITTER: Maslivetc V

PROVIDER: S-EPMC5755969 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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

Maslivetc Vladimir V Barrett Colby C Aksenov Nicolai A NA Rubina Marina M Rubin Michael M

Organic & biomolecular chemistry 20180101 2

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. ...[more]

PMID: 29242861

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