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Synthesis 1999; 1999(4): 669-675
DOI: 10.1055/s-1999-3447
DOI: 10.1055/s-1999-3447
paper
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Synthesis of Racemic and Enantiopure 2-Alkylsulfinyl Dithioacetates and Thioacetamides
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Publication History
Publication Date:
31 December 1999 (online)
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New 2-alkylsulfinyl dithioacetates and thioacetamides have been prepared. The asymmetric synthesis of (R)-2-(cyclohexylsulfinyl)-N,N-dimethylthioacetamide from previously unreported (S)-diacetone-d-glucose cyclohexanesulfinate was achieved in excellent yield (91%) and enantiomeric excess (98%). Methyl (R)-2-(cyclohexylsulfinyl)dithioacetate (98% ee) was obtained from chiral cyclohexyl methyl sulfoxide (99% ee).
sulfoxide - thioamide - dithioester - asymmetric synthesis - chiral sulfinate