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Synfacts 2010(3): 0256-0256  
DOI: 10.1055/s-0029-1219293
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a 3-Aryl-3-trifluoromethyl-2-aminopropanol Derivative

Contributor(s): Philip Kocienski
A. Alimardanov et al.*
Wyeth Research, Pearl River and Princeton, Princeton University, USA and Wyeth Research, Saint-Laurent, Canada
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

The target molecule I of unspecified biological profile was synthesized on a large scale using a chiral auxiliary to control both stereogenic centers via chelation-controlled hydrogenation and α-azidation. An efficient asymmetric hydrogenation of B was also developed ­using an expensive catalyst [Rh(nbd)2BF4 and Walphos 8-1] but the chiral auxiliary route shown was selected for scale up.