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Synfacts 2007(4): 0387-0387
DOI: 10.1055/s-2007-968340
DOI: 10.1055/s-2007-968340
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Synthesis of 1-Aryltrifluoroethylamines
V. L. Truong*, M. S. Ménard, I. Dion
Merck Frosst Centre for Therapeutic Research, Kirkland, Canada
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. März 2007 (online)

Significance
Fluorinated groups adjacent to amines are pharmacologically important for the increased metabolic stability that they provide. Although the yields are modest, the sequence is unique in the operational simplicity and rapidity with which the chiral amines 4 can be obtained. Indeed, both the trifluoroacetaldehyde hydrate (1) and Ellman’s chiral sulfinamide 2 are commercially available, and a one-pot procedure was developed to yield the chiral adduct 3 with excellent selectivity. The mild cleavage conditions released the desired enantiopure amines as the stable HCl salts 4.