Synlett 2011(12): 1660-1667  
DOI: 10.1055/s-0030-1260813
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Organocatalyzed Direct Aldol Additions of Enolizable Aldehydes

Ulf Scheffler, Rainer Mahrwald*
Department of Chemistry, Humboldt University of Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany
Fax: +49(30)20935553; e-Mail: rainer.mahrwald@rz.hu-berlin.de;
Further Information

Publication History

Received 8 March 2011
Publication Date:
05 July 2011 (online)

Abstract

The enantioselective direct cross-aldol addition between enolizable aldehydes is of great importance because this transformation provides access to configurationally defined β-hydroxyaldehydes. These products in turn are valuable building blocks in total syntheses of natural polyketide structures. This account gives an overview of advances made in this field of organocatalysis.

1 Introduction

2 Direct Aldol Additions of Enolizable Aldehydes Catalyzed by Proline, Proline Derivatives, and Imidazolidinone

2.1 Direct Aldol Additions Catalyzed by Proline and Proline Derivatives

2.2 Direct Aldol Additions Catalyzed by Imidazolidinone

3 Direct Aldol Additions of Enolizable Aldehydes Catalyzed by Histidine

4 Conclusion

23

For primary amine catalysis, see: ref. 2a

26

Scheffler, U.; Mahrwald R. in preparation.