T. Takata, Y. Tamura, W. Andō
1985
Citations
0
Influential Citations
23
Citations
Journal
Tetrahedron
Abstract
Abstract Direct hydroxylation α to sulphur was accomplished in singlet oxygenation of thiazolidine derivatives. Photo-oxidation of 4-substituted 3-benzoyl-2,2-dimethylthiazolidines in aprotic solvents below 0° gave the corresponding 5-hydroxy derivatives quantitatively by subsequent treatment of dimethyl sulphide or triphenyl phosphine. The alcohols were stereospecifically formed with 4,5- trans configuration. Protic solvent, such as methanol, inefficiently afforded a mixture of 5-hydroxide and S-oxide. The photo-oxidation of optically active 4-methoxycarbonyl derivative gave the optically active alcohol as only one diastereomer.