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J Am Chem Soc. 2010 Jun 30;132(25):8532-3. doi: 10.1021/ja102832f.

Catalytic asymmetric Roskamp reaction of alpha-alkyl-alpha-diazoesters with aromatic aldehydes: highly enantioselective synthesis of alpha-alkyl-beta-keto esters.

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  • 1Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.

Abstract

The first catalytic enantioselective Roskamp reaction of alpha-alkyl-alpha-diazoesters with aromatic aldehydes was realized using a simple chiral N,N'-dioxide-scandium(III) complex. Remarkably, with 0.05 mol % catalyst, the reaction was performed well over a series of substrates, giving the desired products chemoselectively in excellent yields (up to 99%) and enantioselectivities (up to 98% ee) under mild conditions. This protocol provides a promising method for the synthesis of chiral alpha-alkyl-beta-keto esters and 1,3-diols.

PMID:
20527752
[PubMed]
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