Work

Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides

Year: 2015

Type: article

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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201502341

Authors: Bardia Soltanzadeh, Arvind Jaganathan, Richard J. Staples, Babak Borhan

Institutions: Michigan State University, Dow Chemical (United States)

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G1495357881, Predicted Reaction Discovery and Application of Catalytic Asymmetric Alkene Halogenations, Regio and Stereoselective Reactions in Synthesis of Heterocycles