title: Use of alpha-chlorinated N-(tert-butanesulfinyl)imines in the synthesis of chiral aziridines.
abstract: [reaction: see text] Reaction of chiral alpha-chloro tert-butanesulfinyl aldimines with Grignard reagents efficiently afforded beta-chloro N-sulfinamides in high diastereomeric excess. The latter compounds were cyclized toward the corresponding chiral aziridines in a high-yielding one-pot reaction or after separate treatment with base. The diastereoselectivity obtained in the newly synthesized beta-chloro sulfinamides is explained via the coordinating ability of the alpha-chloro atom with magnesium resulting in the opposite stereochemical outcome as generally observed for nonfunctionalized N-sulfinyl imines.
authors.affiliation: Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Belgium.
authors.forename: Bram
authors.initials: B
authors.lastname: Denolf
authors.forename: Sven
authors.initials: S
authors.lastname: Mangelinckx
authors.forename: Karl W
authors.initials: KW
authors.lastname: Törnroos
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe