title: Stereoselectivity of the Honda-Reformatsky reaction in reactions with ethyl bromodifluoroacetate with α-oxygenated sulfinylimines.
abstract: The Reformatsky reaction of ethyl bromodifluoroacetate to α-oxygenated sulfinylimines is described. Using Honda-Reformatsky conditions, the reaction proceeds with double diastereodifferentiation, with the configuration of the sulfinyl group determining the stereochemical course of the reaction. Excellent diastereoselectivities (>94:6) are obtained for the matched cases. In contrast, reaction with sulfinylimines derived from unsubstituted alkanals proceeded with virtually no diastereoselectivity.
authors.affiliation: Department of Chemistry, University of Southampton , Highfield, Southampton SO17 1BJ, United Kingdom.
authors.forename: Clément Q
authors.initials: CQ
authors.lastname: Fontenelle
authors.forename: Matthew
authors.initials: M
authors.lastname: Conroy
authors.forename: Mark
authors.initials: M
authors.lastname: Light
authors.forename: Thomas
authors.initials: T
authors.lastname: Poisson
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
authors.forename: Bruno
authors.initials: B
authors.lastname: Linclau