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Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides.


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.

SUBMITTER: Soltanzadeh B 

PROVIDER: S-EPMC4874786 | BioStudies | 2015-01-01

REPOSITORIES: biostudies

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