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Mechanism‐Driven Elaboration of an Enantioselective Bromocyclopropanation Reaction of Allylic Alcohols
Author(s) -
Taillemaud Sylvain,
Diercxsens Nicolas,
Gag Alexandre,
Charette André B.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201506083
Subject(s) - allylic rearrangement , enantioselective synthesis , chemistry , reagent , bromide , stereoselectivity , allylic alcohol , ether , combinatorial chemistry , organic chemistry , alcohol , reaction mechanism , mechanism (biology) , catalysis , philosophy , epistemology
A stereoselective bromocyclopropanation of allylic alcohols using dibromomethylzinc bromide is described. Spectroscopic studies to monitor the formation of transient intermediates not only led to the development of a more‐atom‐economical halocyclopropanation reaction, but also highlighted the unique role of ether additives in the process. The desired bromo‐substituted cyclopropanes were isolated in high yields and excellent diastereo‐ as well as enantioselectivities using readily available reagents.