title: Mechanism-Driven Elaboration of an Enantioselective Bromocyclopropanation Reaction of Allylic Alcohols.
abstract: A stereoselective bromocyclopropanation of allylic alcohols using dibromomethylzinc bromide is described. Spectroscopic studies to monitor the formation of transient intermediates not only led to the development of a more-atom-economical halocyclopropanation reaction, but also highlighted the unique role of ether additives in the process. The desired bromo-substituted cyclopropanes were isolated in high yields and excellent diastereo- as well as enantioselectivities using readily available reagents.
authors.affiliation: Department of Chemistry, University of Montreal, P.O. Box 6128 Stn Downtown, Montreal, Quebec, H3C 3J7 (Canada).
authors.forename: Sylvain
authors.initials: S
authors.lastname: Taillemaud
authors.affiliation: Department of Chemistry, University of Montreal, P.O. Box 6128 Stn Downtown, Montreal, Quebec, H3C 3J7 (Canada).
authors.forename: Nicolas
authors.initials: N
authors.lastname: Diercxsens
authors.affiliation: Department of Chemistry, Université du Québec à Montréal, P.O. Box 888, Stn Downtown, Montreal, Quebec, H3C 3P8 (Canada).
authors.forename: Alexandre
authors.initials: A
authors.lastname: Gagnon
authors.affiliation: Department of Chemistry, University of Montreal, P.O. Box 6128 Stn Downtown, Montreal, Quebec, H3C 3J7 (Canada). andre.charette@umontreal.ca.
authors.forename: André B
authors.initials: AB
authors.lastname: Charette
keywords: NMR spectroscopy; carbenoids; cyclopropanes; reaction mechanisms; zinc