Intramolecular Cyclopropanation of 1,4‐Dienes through Hydroboration–Homologation: Easy Access to Bicyclo[3.1.0]hexanes | Zendy

Xu Gong | Zendy; Renaud Philippe | Zendy

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Intramolecular Cyclopropanation of 1,4‐Dienes through Hydroboration–Homologation: Easy Access to Bicyclo[3.1.0]hexanes

Author(s) -

Xu Gong,

Renaud Philippe

Publication year - 2016

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201511100

Subject(s) - cyclopropanation , hydroboration , chemistry , intramolecular force , bicyclic molecule , medicinal chemistry , stereochemistry , organic chemistry , catalysis

An intramolecular cyclopropanation reaction involving B ‐(1‐chloroalkyl)catecholborane intermediates generated from 1,4‐dienes through hydroboration with catecholborane and Matteson homologation was developed. This sequential procedure leading to bicyclo[3.1.0]hexanes involves the formation of three new sigma C−C bonds at the same carbon atom. A mechanistic study supports the involvement of carbocationic intermediates.

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