SYNTHESES OF 3-SUBSTITUTED CHIRAL BORNEOLS AND ISOBORNEOLS AND THEIR ACRYLATES - PRECURSORS FOR PI-FACIAL SELECTIVE REACTIONS

Abstract

A simple synthetic procedure has been described for the syntheses of a few chiral secondary alcohols such as 3-phenylthiomethyl- and 3-phenylsulfonylmethyl-borneols and -isoborneols, potentially useful as chiral auxiliaries. Effect of 3-substitution in these molecules on the proton and carbon resonances has been dehydrochlorination with 1, 8-diazabicyclo[5.4.0]undecene-7 (DBU) has been demonstrated for the formation of acrylates in moderate to very good yields.