Synthesis of unnatural amino acids via Suzuki cross-coupling of enantiopure vinyloxazolidine derivatives.
[formula: see text] (R and S)-alpha-Amino alcohols and alpha-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 alpha-amino alcohols are described.
Sabat
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Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489, USA. crj@chem.wayne.edu
Johnson
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D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D016956:Burkholderia cepacia / Q000201:enzymology; D007700:Kinetics; D008049:Lipase / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
C408869:3-(tert-butoxycarbonyl)-2,2-dimethyl-4-vinyloxazole; C408870:3-benzyloxycarbonyl-2,2-dimethyl-4-vinyloxazole; D000596:Amino Acids; D010080:Oxazoles; D014753:Vinyl Compounds; D008049:Lipase