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A dimethylzinc/diphenylphosphinoylimine approach to the asymmetric synthesis of the calcimimetic agent NPS R-568

✍ Scribed by Sucharita Banerjee; Brad Smith; Shawn R. Hitchcock

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 127 KB
Volume: 25
Category: Article
ISSN: 0268-2605
DOI: 10.1002/aoc.1723

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✦ Synopsis

Abstract

An asymmetric synthesis of the calcimimetic agent NPS R‐568 using a (1__R__,2__S__)‐N‐benzylephedrine‐promoted addition of dimethylzinc to a diphenylphosphinoylimine derived from 3‐methoxybenzaldehyde is described. The enantiomeric ratio of the key amine fragment was determined to be 93:7 (86% ee), favoring the (R)‐enantiomer by derivatization and chiral stationary phase HPLC analysis. Copyright © 2010 John Wiley & Sons, Ltd.

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