Work

Palladium-Catalyzed Asymmetric Allylic Alkylation of 2-Acylimidazoles as Ester Enolate Equivalents

Year: 2010

Type: article

Abstract: A broad range of highly enantioenriched 2-acylimidazoles are synthesized by palladium-catalyzed decarboxylative asymmetric allylic alkylation (DAAA) of 2-imidazolo-substituted enol carbonates. The enantioenriched 2-acylimidazole products can easily be converted to the corresponding carboxylic acid, ester, amide, and ketone derivatives with complete retention of the enantiopurity. The synthetic utility of this new method is demonstrated in the short, efficient synthesis of cetiedil.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja103771w

Authors: Barry M. Trost, Konrad Lehr, David J. Michaelis, Jiayi Xu, Andreas K. Buckl

Institution: Stanford University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Novel Approaches for Antitumor and Antiviral Agents, G38875570, Total Synthesis of Cytotoxic ent-Kauranoid Natural Products