Methods for Synthesis of Chiral Alcohols and Their Conversion to Heterocycles Containing Bi-2-Naphthyl Moiety

Abstract

Convenient methods were developed for the preparation of chiral alcohols containing bi-2-naphthyl moiety in 92–96% yields. The substituted 1,4-diols containing bi-2-naphthyl moiety were further converted to N-substituted pyrrolidine derivatives in 72%-76% yields via the corresponding dimesylate followed by reaction with primary amines. Interestingly, the corresponding chiral tetrahydrofuran derivative was obtained in 90% yield by self condensation of the dimesylate in the absence of primary amines. The results are discussed considering the reaction mechanisms involved in these transformations.