Issue 18, 2011
From the journal:

Organic & Biomolecular Chemistry

A general phosphoric acid-catalyzed desymmetrization of meso-aziridines with silylated selenium nucleophiles†

Matilde Senatore,a   Alessandra Lattanzi,a   Stefano Santoro,b   Claudio Santib  and  Giorgio Della Sala*a  

* Corresponding authors

a Dipartimento di Chimica e Biologia, Università degli Studi di Salerno, Via Ponte Don Melillo, Italy
E-mail: gdsala@unisa.it
Fax: (+)39 089 969603
Tel: (+)39 089 969554

b Dipartimento di Chimica e Tecnologia del Farmaco, Università degli Studi di Perugia, Via del Liceo, Italy

Abstract

The first example of meso-aziridine desymmetrization with selenium nucleophiles is reported. The reaction, promoted by VAPOL-hydrogen phosphate using (phenylseleno)trimethylsilane as the nucleophile, proves to be very general and highly enantioselective (84–99% ee).

Graphical abstract: A general phosphoric acid-catalyzed desymmetrization of meso-aziridines with silylated selenium nucleophiles

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Article information

DOI
https://doi.org/10.1039/C1OB05837A
Article type
Communication
Submitted
26 May 2011
Accepted
12 Jul 2011
First published
12 Jul 2011

Org. Biomol. Chem., 2011,9, 6205-6207

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A general phosphoric acid-catalyzed desymmetrization of meso-aziridines with silylated selenium nucleophiles

M. Senatore, A. Lattanzi, S. Santoro, C. Santi and G. D. Sala, Org. Biomol. Chem., 2011, 9, 6205 DOI: 10.1039/C1OB05837A

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