Stereoselective Transformations of alpha-Trifluoromethylated Ketoximes to Optically Active Amines by Enzyme-Nanometal Cocatalysis: Synthesis of (S)-Inhibitor of Phenylethanolamine N-Methyltransferase

摘要

One-pot cascade synthesis of optically active alpha-trifluoromethylated amines directly from ketoximes was accomplished with the use of Candida antarctica lipase B and catalysts prepared by atomic layer deposition (ALD). Compared to the commercial palladium catalyst, the ALD-prepared catalysts showed much higher activity and afforded various alpha-trifluoromethylated amides in good yields and with high enantioselectivity. One of the enantiopure amides was further hydrolyzed into the corresponding amine, which was treated as a crucial starting material for total synthesis of (S)-inhibitor of phenylethanolamine N-methyltransferase without loss of chiral information.