145655-00-1Relevant articles and documents
2-Thiazolyl α-amino ketones: A new class of reactive intermediates for the stereocontrolled synthesis of unusual amino acids
Dondoni,Perrone
, p. 1162 - 1176 (2007/10/02)
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 C(α), 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).
Homologation of L-phenylalanine to ketomethylene and hydroxyethylene dipeptide isosteres via 2-thiazolyl amino ketone intermediate
Dondoni, Alessandro,Perrone, Daniela
, p. 7259 - 7262 (2007/10/02)
A highly efficient route is presented for the synthesis of N-protected isosteric dipeptides Pheψ[COCH2]Gly and Pheψ[CH(OH)CH2]Phe from L-phenylalanine through 2-thiazolyl α-amino ketone and δ-amino-γ-hydroxy-(E)-α,β-enoate derivative
