Highly enantioselective synthesis of alpha-stereogenic esters through catalytic asymmetric michael addition of 4-oxo-4-arylbutenoates

Chemistry : a European Journal
Zhen WangXiaoming Feng

Abstract

Highly enantioselective Michael addition of 1,3-dicarbonyl compounds and nitromethane to 4-oxo-4-arylbutenoates catalyzed by N,N'-dioxide-Sc(OTf)(3) complexes has been developed. Using 0.5-2 mol % catalyst loading, various alpha-stereogenic esters were obtained regioselectively with excellent yields (up to 97 %) and enantioselectivities (up to >99 % ee). Moreover, the reaction performed well under nearly solvent-free conditions. The products with functional groups are ready for further transformation, which showed the potential value of the catalytic approach. According to the experimental results and previous reports, a plausible working model has been proposed to explain the origin of the activation and the asymmetric induction.

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Citations

Sep 29, 2012·Beilstein Journal of Organic Chemistry·Sergei ZariTõnis Kanger
Jan 23, 2014·Organic & Biomolecular Chemistry·Suckchang HongHyeung-geun Park
Jun 20, 2012·Organic Letters·G K Surya PrakashGeorge A Olah

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