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Highly Stereoselective Halocyclopropanation of α,β‐Unsaturated Amides
Author(s) -
Concellón José M.,
RodríguezSolla Humberto,
Blanco Elena G.,
VillaGarcía María A.,
Alvaredo Noemí,
GarcíaGranda Santiago,
Díaz M. Rosario
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900331
Subject(s) - stereoselectivity , chemistry , chromium , transformation (genetics) , stereochemistry , organic chemistry , catalysis , biochemistry , gene
A convenient highly stereoselective synthesis of chloro‐ and bromocyclopropanamides from di‐ tri‐ or tetrasubstituted ( E )‐ or ( Z )‐α,β ‐ unsaturated amides with total or high stereoselectivity promoted by chromium dichloride or dibromide is described. The transformation of chlorocyclopropanamides into the corresponding ketones or amines is also reported. A mechanism to explain these transformations is proposed.