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Use of alpha-chlorinated N-(tert-butanesulfinyl)imines in the synthesis of chiral aziridines.

Organic letters (2006-06-30)
Bram Denolf, Sven Mangelinckx, Karl W Törnroos, Norbert De Kimpe
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(R)-(+)-2-Methyl-2-propanesulfinamide, 98%

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