- Organocatalytic Michael-Knoevenagel-hetero-Diels-Alder reactions: an efficient asymmetric one-pot strategy to isochromene pyrimidinedione derivatives.
Organocatalytic Michael-Knoevenagel-hetero-Diels-Alder reactions: an efficient asymmetric one-pot strategy to isochromene pyrimidinedione derivatives.
Organic letters (2011-12-27)
Bor-Cherng Hong, Nitin S Dange, Chun-Feng Ding, Ju-Hsiou Liao
PMID22195677
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.
MATERIALS