title: Diastereoselective alkylations of a protected cysteinesulfenate.
abstract: To further understand stereoselection in the alkylation of sulfenate anions, a protected cysteinesulfenate was generated in THF solution at low temperature. Introduction of a reactive alkylating agent brings about a cysteinyl sulfoxide in 51-75% yield, with diastereomeric ratios at the sulfinyl group ranging from 83:17 to 95:5. An internally complexed lithium counterion is proposed to account for the stereoselectivity.
authors.affiliation: Department of Chemistry, University of Guelph, Guelph, Ontario, Canada, N1G 2W1. schwan@uoguelph.ca
authors.forename: Adrian L
authors.initials: AL
authors.lastname: Schwan
authors.forename: Marcus J
authors.initials: MJ
authors.lastname: Verdu
authors.forename: Suneel P
authors.initials: SP
authors.lastname: Singh
authors.forename: Jennifer S
authors.initials: JS
authors.lastname: O'Donnell
authors.forename: Amir Nasser
authors.initials: AN
authors.lastname: Ahmadi