Tetrahedron letters

Efficient synthesis of chiral phenethylamines: preparation, asymmetric hydrogenation, and mild deprotection of ene-trifluoroacetamides

SP Allwein, JC McWilliams, EA Secord, DR Mowrey…

Index: Allwein, Shawn P.; McWilliams, J. Christopher; Secord, Elizabeth A.; Mowrey, Dale R.; Nelson, Todd D.; Kress, Michael H. Tetrahedron Letters, 2006 , vol. 47, # 36 p. 6409 - 6412

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Citation Number: 19

Abstract

A mild and efficient route to enantioenriched aryl alkyl amines from ketones has been developed. The first successful synthesis and asymmetric hydrogenation of ene- trifluoroamides from oximes gave highly enantioenriched trifluoroacetamides (94–98% ee). The corresponding phenethyl amides are liberated under mild conditions (K2CO3, MeOH/H2O). In addition, a new application of Josiphos ligands toward the asymmetric ...