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Catalytic asymmetric reductive amination of ketones via highly enantioselective hydrogenation of the CN double bond by Mark J. Burk; Jose P. Martinez; John E. Feaster; Nick Cosford is a Chemistry article available to read on EtoBox.

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We describe a convenient, chemoselective asymmetric reductive amination procedure for the conversion of ketones to chiral hydrazines and amines. The key step in the three-step process is enantioselective DuPHOS-Rh-catalyzed hydrogenation of the C=N double bond of N-acylhydrarones. Detailed optimization studies revealed the effect of solvent, temperature, and the N-acyl group on the enantioselectivity and catalytic efficiency of the reaction. The reduction products, N-acylhydrazines, were converted to hydratines or amines through hydrolysis or treatment with samarium(U) iodide, respectively.

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Author

Mark J. Burk; Jose P. Martinez; John E. Feaster; Nick Cosford

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

1994

Language

EN

Field

Chemistry (Physical Sciences)