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Synthesis 1993; 1993(11): 1162-1176
DOI: 10.1055/s-1993-26021
DOI: 10.1055/s-1993-26021
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2-Thiazolyl α-Amino Ketones: A New Class of Reactive Intermediates for the Stereocontrolled Synthesis of Unusual Amino Acids
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Publication History
Publication Date:
29 April 2002 (online)
The thiazole-based one carbon homologation of four α-amino acids (L-phenylalanine, L-leucine, L-threonine, and L-serine) to the corresponding α-hydroxy β-amino aldehydes and acids in both configurations at Cα, is described. The methodology involves the following key operations: (i) the conversion of an α-amino ester to a 2-thiazolyl α-amino ketone; (ii) the stereocontrolled reduction of a ketone carbonyl to either syn or anti α,β-amino alcohols; (iii) the aldehyde release from the thiazole ring; (iv) the oxidation of the aldehyde to a carboxylic acid. The methodology was only partially applied to L-phenylglycine because of some limitations in operation (i).