Organic Letters 2012-01-20

Organocatalytic Michael-Knoevenagel-hetero-Diels-Alder reactions: an efficient asymmetric one-pot strategy to isochromene pyrimidinedione derivatives.

Bor-Cherng Hong, Nitin S Dange, Chun-Feng Ding, Ju-Hsiou Liao

Index: Org. Lett. 14(2) , 448-51, (2012)

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Abstract

Synthesis of isochromene pyrimidinedione derivatives having five stereocenters has been achieved by a one-pot Michael-Knoevenagel condensation-inverse-electron-demand hetero-Diels-Alder reaction of α, β-unsaturated aldehydes, olefinic nitroalkanes, and 1,3-dimethylbarbituric acid via a one-pot strategy with excellent diastereo- and enantioselectivities (up to 99% ee). The structures and absolute configurations of the products were confirmed by X-ray analysis.© 2011 American Chemical Society