Design of Modified Amine Transfer Reagents Allows the Synthesis of α-Chiral Secondary Amines via CuH-Catalyzed Hydroamination
Dawen Niu and Stephen L. Buchwald*
*Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu
D. Niu, S. L. Buchwald, J. Am. Chem. Soc., 2015, 137, 9716-9721.
DOI: 10.1021/jacs.5b05446 (free Supporting Information)
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A CuH-catalyzed hydroamination of alkenes using an amine transfer reagent and a silane provides chiral amines with high efficiency and stereoselectivity. However, the current technology has been limited to dialkylamine transfer reagents (R2NOBz). A modified type of monoalkylamine transfer enabled the synthesis of chiral secondary amines, including those derived from amino acid esters, carbohydrates, and steroids.
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