An Enantioselective Synthesis of (<i>S</i>)-(+)-3-Aminomethyl-5-methylhexanoic Acid via Asymmetric Hydrogenation

J. Burk, Mark; D. de Koning, Pieter; M. Grote, Todd; S. Hoekstra, Marvin; Hoge, Garrett; A. Jennings, Rex; S. Kissel, William; Le, Tung; C. Lennon, Ian; A. Mulhern, Thomas; A. Ramsden, James; A. Wade, Robert

doi:10.1021/jo034397b

Public

An Enantioselective Synthesis of (S)-(+)-3-Aminomethyl-5-methylhexanoic Acid via Asymmetric Hydrogenation

Published in The Journal of Organic Chemistry • Jun 6, 2003

Authors:

Mark J. Burk

Pieter D. de Koning

Todd M. Grote

Abstract

A concise enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid (1, Pregabalin) has been developed. The key step is the asymmetric hydrogenation of a 3-cyano-5-methylhex-3-enoic acid salt 2 with a rhodium Me-DuPHOS catalyst, providing the desired (S)-3-cyano-5-methylhexanoate 3 i...

Subject

Enantioselective synthesis

Chemistry

Nitrile

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