Pj. Nadkarni et al., SYNTHESES OF 3-SUBSTITUTED CHIRAL BORNEOLS AND ISOBORNEOLS AND THEIR ACRYLATES - PRECURSORS FOR PI-FACIAL SELECTIVE REACTIONS, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 34(6), 1995, pp. 474-483
A simple synthetic procedure has been described for the syntheses of a
few chiral secondary alcohols such as 3-phenylthiomethyl- and 3-pheny
lsulfonylmethyl-borneols and -isoborneols, potentially useful as chira
l auxiliaries. Effect of 3-substitution in these molecules on the prot
on and carbon resonances has been dehydrochlorination with 1, 8-diazab
icyclo[5.4.0]undecene-7 (DBU) has been demonstrated for the formation
of acrylates in moderate to very good yields.