Polymer-Aided Stereodivergent Synthesis (PASS): A New Concept for the Discrete Preparation of Optical Antipodes
2001; American Chemical Society; Volume: 3; Issue: 7 Linguagem: Inglês
10.1021/ol015723h
ISSN1523-7060
AutoresPeter ten Holte, L. Thijs, B. Zwanenburg,
Tópico(s)Synthetic Organic Chemistry Methods
Resumo[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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