ChemInform Abstract: Synthesis of Chiral Sulfines by Oxidation of Dithio Esters.

Abstract

1995 sulfoxides, sulfones, sulfenes and derivatives sulfoxides, sulfones, sulfenes and derivatives (acyclic compounds) P 0450 -102Synthesis of Chiral Sulfines by Oxidation of Dithio Esters.-The oxidation of chiral sulfines bearing different substituents at C-. alpha. is carried out and the chiral integrity of the stereogenic center is studied. The sulfine bearing an amido group, compound (II), is stabilized by intramolecular hydrogen bonding and does not racemize. When C-α in the sulfine bears an acetoxy group, a rearrangement to a mixture of S-methyl ester (VI) and dithioperoxy ester (VII) takes place but the optical activity remains unchanged. With an alkyl group at C-α the sulfines (IX) and (X) undergo a fast racemization and rearrange to a mixture of (XI), (XII) and (XIII). -(VAN DER LINDEN, J. B.; TIMMERMANS, J. L.; ZWANENBURG, B.; Recl. Trav. Chim. Pays-Bas 114 (1995) 3, 91-96; Dep. Org. Chem., Univ., NL-6525 ED Nijmegen, Neth.; EN)