Polymer-aided stereodivergent synthesis (PASS): a new concept for the discrete preparation of optical antipodes |
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Authors: | ten Holte P Thijs L Zwanenburg B |
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Institution: | 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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Abstract: | 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. |
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