484689-80-7Relevant articles and documents
Synthesis of an enantiomerically pure 1,3-thiazole-5(4H)-thione and its stereoselective 1,3-dipolar cycloaddition with an azomethine ylide
Gebert, Andreas,Heimgartner, Heinz
, p. 2073 - 2082 (2007/10/03)
Starting from the enantiomerically pure 2H-azirin-3-amines (R,S)-4 and (S,S)-4, the enantiomeric, optically active 4-benzyl-4-methyl-2-phenyl-1,3-thiazole-5(4H)-thiones (R)-1 and (S)-1, respectively, have been prepared (Schemes 2 and 3). In each case, the
Optically active 3-amino-2H-azirines as synthons for enantiomerically pure α,α-disubstituted α-amino acids: Synthesis of the α-methylphenylalanine synthons and some model peptides
Bucher,Linden,Heimgartner
, p. 935 - 946 (2007/10/02)
The synthesis of a novel 2-benzyl-2-methyl-3-amino-2H-azirine derivative with a chiral amino group is described. Chromatographic separation of the diastereoisomer mixture yielded the pure diastereoisomers 9a and 9b which are the D- and L-2-methylphenylalanine ((α-Me)Phe) synthons, respectively. The reaction of 9a and 9b with thiobenzoic acid and with Z-leucine yielded the monothiodiamides 10a and 10b and the dipeptide derivatives 11a and 11b, respectively. Methanolysis of 11b yielded 12b. The absolute configuration of 10a was established by X-ray crystallography. The absolute configuration of (α-Me)Phe in 12b has been deduced from the known configuration of L-leucine.
