Synlett 2008(10): 1574-1578  
DOI: 10.1055/s-2008-1078410
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© Georg Thieme Verlag Stuttgart · New York

Zn(II)-Catalyzed Desymmetrization of meso-Epoxides by Aromatic Amines in Water

Simona Bonollo, Francesco Fringuelli*, Ferdinando Pizzo*, Luigi Vaccaro
Dipartimento di Chimica, Università di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italia
Fax: +39(075)5855560; e-Mail: frifra@unipg.it;
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Publikationsverlauf

Received 27 December 2007
Publikationsdatum:
16. Mai 2008 (online)

Abstract

The Zn(OTf)2-SDS-bipyridine 1 system has proved to be an effective catalyst in water for the desymmetrization of epoxides 2a-d by anilines 3a-d. After obtaining comparable results by using Sc(III)-SDS and Zn(II)-SDS systems in the case of 2a and 3a, we have explored the enantioselective ring opening of small epoxides for which water has never been used as reaction medium. Up to date the 85% ee obtained in the case of cyclohexene oxide 2b with amines 3a and 3d are very good results and are the highest values obtained in water as reaction medium.