New synthetic utility of singlet oxygen in sulphide photo-oxidation

Add time:08/04/2019    Source:sciencedirect.com

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.

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