Work

Dramatic Improvement of the Enantiomeric Excess in the Asymmetric Conjugate Addition Reaction Using New Experimental Conditions

Year: 2002

Type: article

Abstract: The asymmetric conjugate addition of dialkylzincs is usually performed with Cu(OTf)(2) in toluene. We show that by using a copper carboxylate in Et(2)O, THF, or EtOAc, we strongly improve the enantioselectivity with a given ligand. Ee values up to 99.1% could be reached with new ligands based on the induced atropisomerism of a simple biphenol unit. In addition, we show that the Lewis acid effect of Cu(OTf)(2) is not a significant.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja025598k

Authors: A. Alexakis, C. Benhaim, S. Rosset, M. Humam

Institution: University of Geneva

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

OpenAlex ID: W2007884545

FWCI: 23.21

Cites: 21

Cited by: 278

Related to: 9