Synthesis of racemic and enantiopure 2-alkylsulfinyl dithioacetates and thioacetamides

Authors
Alayrac, C Nowaczyk, S Lemarie, M Metzner, P
Citation
C. Alayrac et al., Synthesis of racemic and enantiopure 2-alkylsulfinyl dithioacetates and thioacetamides, SYNTHESIS-S, (4), 1999, pp. 669-675
Citations number
61
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
4
Year of publication
1999
Pages
669 - 675
Database
ISI
SICI code
0039-7881(199904):4<669:SORAE2>2.0.ZU;2-O
Abstract
New 2-alkylsulfinyl dithioacetates and thioacetamides have been prepared. T he asymmetric synthesis of (R)-2-(cyclohexylsulfinyl)-N,N-dimethylthioaceta mide from previously unreported (S)-diacetone-D-glucose cyclohexanesulfinat e was achieved in excellent yield (91%) and enantiomeric excess (98%). Meth yl (R)-2- (cyclohexylsulfinyl)dithioacetate (98% ee) was obtained from chir al cyclohexyl methyl sulfoxide (99% ee).