Theory of asymmetric organocatalysis of Aldol and related reactions: rationalizations and predictions

Christophe Allemann; Ruth Gordillo; Fernando R Clemente; Paul Ha-Yeon Cheong; K N Houk

doi:10.1021/ar0300524

Theory of asymmetric organocatalysis of Aldol and related reactions: rationalizations and predictions

Acc Chem Res. 2004 Aug;37(8):558-69. doi: 10.1021/ar0300524.

Authors

Christophe Allemann¹, Ruth Gordillo, Fernando R Clemente, Paul Ha-Yeon Cheong, K N Houk

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.

PMID: 15311955
DOI: 10.1021/ar0300524

Abstract

Computational studies have led to models to understand some classic and contemporary asymmetric reactions involving organocatalysts. The Hajos-Parrish-Eder-Sauer-Wiechert reaction and intermolecular aldol reactions as well as Mannich reactions and oxyaminations catalyzed by proline and other amino acids, and Diels-Alder reactions catalyzed by MacMillan's chiral amine organocatalysts have been studied with density functional theory. Quantitative predictions for several new catalysts and reactions are provided.