Synthesis of unnatural amino acids via Suzuki cross-coupling of enantiopure vinyloxazolidine derivatives

(R and S)-alpha-Amino alcohols and alpha-amino acids, including 4-methoxyho mophenylalanine, with a variety of unnatural side chains have been synthesi zed via palladium-catalyzed cross coupling Suzuki reactions. The key buildi ng blocks 1 and 2, synthesized from the common achiral precursor 2-butene-1 ,4-diol, were made enantiopure utilizing a Pseudomonas cepacia lipase-catal yzed kinetic resolution. The optimal conditions for the Suzuki cross-coupli ng and the subsequent oxidations of the resultant alpha-amino alcohols are described.