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Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides
Author(s) -
Soltanzadeh Bardia,
Jaganathan Arvind,
Staples Richard J.,
Borhan Babak
Publication year - 2015
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.201502341
Subject(s) - alkene , chemistry , enantioselective synthesis , halogenation , stereoselectivity , intermolecular force , nucleophile , catalysis , organic chemistry , combinatorial chemistry , molecule
Abstract An organocatalytic and highly regio‐, diastereo‐, and enantioselective intermolecular haloetherification and haloesterification reaction of allyl amides is reported. A variety of alkene substituents and substitution patterns are compatible with this chemistry. Notably, electronically unbiased alkene substrates exhibit exquisite regio‐ and diastereoselectivity for the title transformation. We also demonstrate that the same catalytic system can be used in both chlorination and bromination reactions of allyl amides with a variety of nucleophiles with little or no modification.