Enantioselective Oxidation of Thioethers: Synthesis of trans-2-N,N-Dialkylacetamide-1,3-dithiolanes-S-oxide and Their Use in Asymmetric Aldol-Type Reactions

Article abstract of DOI:10.1016/S0040-4039(00)79595-5

(-)-trans-2-N,N-dialkylacetamide-1,3-dithiolanes-S-oxide 2 have been obtained in high d.e. (>99:1) and e.e.(up to 94percent, >98percent after crystallization) by enantioselective oxidation .The aldol-type addition of the magnesium enolate of the N,N-diethyl derivative (-)-2b to iso-butyraldehyde afforded good chemical yields of a single diastereomer.Key Words: Enantioselective oxidation; Asymmetric aldol-type addition, trans-(-)-2-N,N-Diethylacetamide-1,3-dithiolane-S-oxide.