title: Highly Regio- and Enantioselective Vicinal Dihalogenation of Allyl Amides.
abstract: We report a highly regio-, diastereo- and enantioselective vicinal dihalogenation of allyl amides. E- and Z-alkenes with both aryl and alkyl substituents were compatible with this chemistry. This is the result of exquisite catalyst controlled regioselectivity enabling use of electronically unbiased substrates. The reaction employs commercially available catalysts and halenium sources along with cheap inorganic halide salts to affect this transformation. A preliminary effort to extend this chemistry to heterodihalogenation is also presented.
authors.affiliation: Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.
authors.forename: Bardia
authors.initials: B
authors.lastname: Soltanzadeh
authors.affiliation: Dow Agrosciences LLC , 9330 Zionsville Road, Indianapolis, Indiana 46268, United States.
authors.forename: Arvind
authors.initials: A
authors.lastname: Jaganathan
authors.affiliation: Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.
authors.forename: Yi
authors.initials: Y
authors.lastname: Yi
authors.affiliation: Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.
authors.forename: Hajoon
authors.initials: H
authors.lastname: Yi
authors.affiliation: Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Staples
authors.affiliation: Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.
authors.forename: Babak
authors.identifier: 0000-0002-3193-0732
authors.initials: B
authors.lastname: Borhan
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D054879:Halogenation; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D000577:Amides; D006846:Hydrocarbons, Halogenated