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Synthesis 2011(12): 1815-1830  
DOI: 10.1055/s-0030-1260029
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Developing Novel Organocatalyzed Aldol Reactions for the Enantioselective Synthesis of Biologically Active Molecules

Mayur Bhanushali, Cong-Gui Zhao*
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249-0698, USA
Fax: +1(210)4587428; e-Mail: cong.zhao@utsa.edu;
Further Information

Publication History

Received 14 March 2011
Publication Date:
06 May 2011 (online)

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Abstract

The aldol reaction is one of the most important methods for the formation of carbon-carbon bonds. Because of its significance and utility, asymmetric versions of this reaction have been realized with different approaches in the past. Over the last decade, the area of organocatalysis has made significant progress. As one of most studied reactions in organocatalysis, the organocatalyzed aldol reaction has emerged as a powerful tool for the synthesis of a large number of useful products in optically enriched forms. In this review, we summarize our efforts on the development of novel organocatalyzed aldol reactions for the enantioselective synthesis of biologically active molecules.

1 Introduction

2 Enamine-Mediated Aldol Reactions

2.1 Design and Synthesis of C 2-Symmetric Bisprolinamides for Asymmetric Aldol Reactions

2.2 Aldol Reaction of 1,2-Diketones and Glyoxylates

2.3 Synthesis of α-Hydroxy Phosphonates and Phosphinates

3 Enolate- and Enol-Mediated Aldol Reactions of Unactivated Ketones

4 Organocatalytic Tandem Reactions

5 Conclusion

Key words

aldol reaction - carbonyl compounds - proline - cinchona alkaloid thioureas - organocatalysis