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

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Abstract

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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ligand

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Key Words

benzyl amines, diethoxymethylsilane, CuH

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ID: J48-Y2015