Polymer-aided stereodivergent synthesis (PASS): A new concept for the discrete preparation of optical antipodes

Authors
ten Holte, P Thijs, L Zwanenburg, B
Citation
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
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
7
Year of publication
2001
Pages
1093 - 1095
Database
ISI
SICI code
1523-7060(20010405)3:7<1093:PSS(AN>2.0.ZU;2-K
Abstract
[GRAPHICS] 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.