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CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines

Haoxuan Wang, Jeffrey C. Yang and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu

H. Wang, J. C. Yang, S. L. Buchwald, J. Am. Chem. Soc., 2017, 139, 8428-8431.

DOI: 10.1021/jacs.7b04816 (free Supporting Information)



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Abstract

In a direct route for the synthesis of alkyl-substituted chiral aziridines from achiral starting materials, readily accessed allylic hydroxylamine esters undergo copper hydride-catalyzed intramolecular hydroamination with a high degree of regio- and enantiocontrol to afford the aziridine products in good to excellent yields in highly enantioenriched form.

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Key Words

aziridines, dimethoxymethylsilane


ID: J48-Y2017