Asymmetric Synthesis of α‐Phenyl‐γ‐hetero‐substituted Isopropyl Sulfonates via Diastereoselective Ring‐Opening of γ‐Sultones.

Abstract

Ring opening reactions O 0132Asymmetric Synthesis of α-Phenyl-γ-hetero-substituted Isopropyl Sulfonates via Diastereoselective Ring-Opening of γ-Sultones. -The ring opening of sultone (I) with various heteronucleophiles is performed smoothly in DMF or DMSO as solvent under anhydrous conditions, without epimerization at the α-position of the sulfonyl group. The asymmetric access to sulfonates (IV), (VI), (VIII), (X), and (XI) is achieved via a simple three-step reaction sequence in very good overall yields (65-86%) and excellent diastereo-and enantiomeric selectivities. -(ENDERS*, D.; IFFLAND, D.; Synthesis 2007Synthesis , 12, 1837Synthesis -1840 Inst. Org. Chem.,