Chemo-enzymatic synthesis of chiral fluorine-containing building blocks

Abstract

Two complementary strategies for the synthesis of optically active fluorine-containing building blocks have been probed. The first strategy involves either the enzymatic resolution of fluorinated α,α- disubstituted-α-amino acid amides, or the asymmetric hydrogenation of fluorinated dehydroamino acids. The second strategy involves the transition metal-catalyzed introduction of fluorine-containing substituents onto olefin- or acetylene-containing α-H-α-amino acids. These amino acids in turn are made optically active by enzymatic resolution of the corresponding amides.