Use of alpha-Chlorinated N-(tert-Butanesulfinyl)imines in the Synthesis of Chiral Aziridines.
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Use of alpha-Chlorinated N-(tert-Butanesulfinyl)imines in the Synthesis of Chiral Aziridines.
Org Lett. 2006 Jul 6;8(14):3129-32
Authors: Denolf B, Mangelinckx S, Törnroos KW, De Kimpe N
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.
PMID: 16805569 [PubMed - in process]
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