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Synthesis 1999; 1999(4): 669-675
DOI: 10.1055/s-1999-3447
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Synthesis of Racemic and Enantiopure 2-Alkylsulfinyl Dithioacetates and Thioacetamides

Carole Alayrac* , Stéphanie Nowaczyk, Margareth Lemarié, Patrick Metzner
  • *Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS n° 6507), ISMRA-Université, 6 boulevard du Maréchal Juin, F-14050 Caen, France; Fax +33(2)31 45 28 77; E-mail: alayrac@ismra.fr
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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

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