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Updated: Jul 17, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Asymmetric synthesis of cyclopropylamines starting from N-sulfinyl alpha-chloro ketimines
Bram Denolf1, Sven Mangelinckx, Karl W Törnroos
1Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Abstract:
Treatment of novel chiral N-sulfinyl alpha-chloro ketimines with Grignard reagents resulted in the synthesis of chiral N-(1-substituted cyclopropyl)-tert-butanesulfinamides in acceptable to good yields and diastereoselectivity via 1,3-dehydrohalogenation and subsequent addition of the Grignard reagent to the intermediate cyclopropylideneamine. Only in the case of allylmagnesium chloride did the reaction lead to aziridines in high yield. Further deprotection toward N-unprotected 1-substituted cyclopropylamines was established, and the absolute configuration was determined. [reaction: see text].
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