title: 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.
authors.affiliation: Department of Chemistry, Michigan State University, E. Lansing, MI 48824 (USA).
authors.forename: Bardia
authors.initials: B
authors.lastname: Soltanzadeh
authors.affiliation: Engineering and Process Sciences, Core R&D, The Dow Chemical Company, Midland, MI 48674 (USA).
authors.forename: Arvind
authors.initials: A
authors.lastname: Jaganathan
authors.affiliation: Department of Chemistry, Michigan State University, E. Lansing, MI 48824 (USA).
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Staples
authors.affiliation: Department of Chemistry, Michigan State University, E. Lansing, MI 48824 (USA). babak@chemistry.msu.edu.
authors.forename: Babak
authors.initials: B
authors.lastname: Borhan
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D004951:Esterification; D004987:Ethers / Q000737:chemistry*; D054879:Halogenation; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D000577:Amides; D004987:Ethers
keywords: chloroetherification; enantioselectivity; halogenation; organocatalysis; regioselectivity