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Use of α-Chlorinated N-(tert-Butanesulfinyl)imines in the Synthesis of Chiral Aziridines

Bram Denolf, Sven Mangelinckx, Karl W. Törnroos and Norbert De Kimpe*

*Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium, Email: norbert.dekimpeugent.be

B. Denolf, S. Mangelinckx, K. W. Törnroos, N. De Kimpe, Org. Lett., 2006, 8, 3129-3132.

DOI: 10.1021/ol0611245 (free Supporting Information)


Abstract

Reaction of chiral α-chloro tert-butanesulfinyl aldimines with Grignard reagents efficiently afforded β-chloro N-sulfinamides in high diastereomeric excess. A subsequent base-mediated cyclization yielded chiral aziridines. The coordinating ability of the α-chloro atom with magnesium results in the opposite stereochemical outcome as generally observed for nonfunctionalized N-sulfinyl imines.

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Key Words

De Kimpe Aziridine Synthesis


ID: J54-Y2006-4930