Synlett 2005(5): 0875-0876  
DOI: 10.1055/s-2005-864796
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Cinchona Alkaloid Derivatives as Chiral Organocatalysts

Ciarán Ó Dálaigh*
Department of Organic Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland
e-Mail: odalaigc@tcd.ie;
Further Information

Publication History

Publication Date:
10 March 2005 (online)

Introduction

The last five years have witnessed a resurgence of interest in the cinchona alkaloids [1] [e.g. Quinine (1) and Quinidine (2)] due to their potential to serve as air- and moisture-insensitive asymmetric organocatalysts for a variety of enantioselective transformations. These materials are of particular synthetic utility as they are inexpensive, readily available natural products and are obtainable in either of their pseudo-enantiomeric forms. In addition to ready availability, cinchona alkaloids also possess both Lewis acidic (H-bonding) and Lewis basic (quinuclidine nitrogen) sites, thus making them potentially useful for the promotion of a variety of reactions via bifunctional catalysis.

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