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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-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides.

Soltanzadeh Bardia B Jaganathan Arvind A Staples Richard J RJ Borhan Babak B

Angewandte Chemie (International ed. in English) 20150625 33

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 reaction ...[more]

PMID: 26110812

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