Literature DB >> 20550121

Palladium-catalyzed asymmetric allylic alkylation of 2-acylimidazoles as ester enolate equivalents.

Barry M Trost1, Konrad Lehr, David J Michaelis, Jiayi Xu, Andreas K Buckl.   

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.

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Year:  2010        PMID： 20550121      PMCID： PMC2908042          DOI： 10.1021/ja103771w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  13 in total

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