Asymmetric Synthesis of α-Phenyl-γ-Hetero-Substituted Isopropyl Sulfonates via Diastereoselective Ring-Opening of γ-Sultones

Abstract

An efficient route to α-phenyl-γ-hetero (O, S, Se, Cl)-substituted isopropyl sulfonates via S_N2-ring opening of γ-sultones, easily available by asymmetric synthesis from chiral lithiated sulfonates, is described. The title compounds are obtained in very good overall yields of 65-86% over three steps and excellent diastereo- and enantiomeric excesses (de = 94-96%, ee ≥ 98%).

Key words

sultones - sulfonates - asymmetric synthesis - ring-opening - heteronucleophiles

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