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Catalytic Asymmetric Roskamp Reaction of α-Alkyl-α-diazoesters with Aromatic Aldehydes: Highly Enantioselective Synthesis of α-Alkyl-β-keto Esters

2010; American Chemical Society; Volume: 132; Issue: 25 Linguagem: Inglês

10.1021/ja102832f

1943-2984

Wei Li, Jun Wang, Xiaolei Hu, Ke Shen, Wentao Wang, Yangyang Chu, Lili Lin, Xiaohua Liu, Xiaoming Feng,

Asymmetric Synthesis and Catalysis

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.