Synthesis of unnatural amino acids via suzuki cross-coupling of enantiopure vinyloxazolidine derivatives
(R and S)-α-Amino alcohols and α-amino acids, including 4-methoxyhomophenylalanine, with a variety of unnatural side chains have been synthesized via palladium-catalyzed cross-coupling Suzuki reactions. The key building blocks 1 and 2, synthesized from the common achiral precursor 2-butene-1,4-diol, were made enantiopure utilizing a Pseudomonas cepacia lipase-catalyzed kinetic resolution. The optimal conditions for the Suzuki cross-coupling and the subsequent oxidations of the resultant α-amino alcohols are described.
Sabat, Mark,Johnson, Carl R.
p. 1089 - 1091
(2007/10/03)
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