Concise synthesis of enantiopure alpha-trifluoromethyl alanines, diamines, and amino alcohols via the Strecker-type reaction.

Florent Huguenot, Thierry Brigaud

Index: J. Org. Chem. 71 , 7075, (2006)

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Abstract

Diastereomerically pure alpha-trifluoromethyl alpha-amino nitriles obtained by Strecker-type reactions from chiral CF3 imines and iminium proved to be very attractive versatile intermediates for the synthesis of various alpha-trifluoromethyl amino compounds. From these synthons, both enantiomers of alpha-trifluoromethyl alanine, trifluoromethyl 1,2-diamines, and amino alcohols were conveniently obtained in enantiopure form in high yields in a few steps.