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 ?,?-disubstituted-?-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 ?-H-?-amino acids. These amino acids in turn are made optically active by enzymatic resolution of the corresponding amides.

Keywords

• Asymmetric hydrogenation
• Chiral building blocks
• Enzymatic resolution
• Fluorinated amino acids
• Transition metal catalysis