Synthesis 2005(9): 1431-1436  
DOI: 10.1055/s-2005-865313
PAPER
© Georg Thieme Verlag Stuttgart · New York

Enantio- and Diastereoselective [3+2] Cycloadditions of Azomethine Ylides with Ag(I)-Phosphinooxazoline Catalysts

Remo Stohler, Florentine Wahl, Andreas Pfaltz*
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland
e-Mail: andreas.pfaltz@unibas.ch;
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Publikationsverlauf

Received 1 March 2005
Publikationsdatum:
18. April 2005 (online)

Abstract

Chiral Ag(I)-phosphinooxazoline (PHOX) complexes are efficient catalysts for [3+2] cycloadditions of azomethine ylides with α,β-unsaturated carboxylic esters. In intramolecular cycloadditions, virtually complete diastereocontrol and enantiomeric excesses of up to 99% have been observed.