Polymer-aided stereodivergent synthesis (PASS): a new concept for the discrete preparation of optical antipodes.
[structure: see text]. 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 leads to the formation and separation of quasi-enantiomers 2 and 3 simultaneously, with one being immobilized and one free in solution. Treatment of 2 and 3 with appropriate nucleophiles gives discrete enantiomers 4 and 5.
Department of Organic Chemistry, NSR Institute for Molecular Structure, Design and Synthesis, University of Nijmegen, Toernooiveld, 6525 ED Nijmegen, The Netherlands.
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ten Holte
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Thijs
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Zwanenburg