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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.