Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides |
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| Authors: | Bardia Soltanzadeh Dr. Arvind Jaganathan Dr. Richard J. Staples Prof. Dr. Babak Borhan |
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| Affiliation: | 1. Department of Chemistry, Michigan State University, E. Lansing, MI 48824 (USA);2. Engineering and Process Sciences, Core R&D, The Dow Chemical Company, Midland, MI 48674 (USA) |
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| 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. |
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| Keywords: | chloroetherification enantioselectivity halogenation organocatalysis regioselectivity |
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