P. Ten Holte et al., Polymer-aided stereodivergent synthesis (PASS): A new concept for the discrete preparation of optical antipodes, ORG LETT, 3(7), 2001, pp. 1093-1095
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A new concept for the discrete preparation of optical antipodes is reported
. The approach makes use of a cyclization/cleavage procedure that has been
applied to polymer-supported quasi-meso compound 1, containing a polymeric
leaving group and a regular leaving group. Two-directional cyclization lead
s to the formation and separation of quasi-enantiomers 2 and 3 simultaneous
ly, with one being immobilized and one free in solution. Treatment of 2 and
3 with appropriate nucleophiles gives discrete enantiomers 4 and 5.