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Cascade Michael/aldol/rearrangement between phenacylmalononitriles and maleimides: highly diastereoselective access to functionalized bicyclic cyclopentenes containing a CN-substituted all-carbon quaternary center†‡
Li Gao,Gaihui Li,Xiaokang Li,Guoshun Zhang,Min Zhang,Shurong Ban
Organic Chemistry Frontiers Pub Date : 03/19/2022 00:00:00 , DOI:10.1039/D1QO01762D
Abstract

Annulation of phenacylmalononitriles with maleimides offers a highly diastereoselective synthesis of unprecedented multifunctionalized bicyclic cyclopentenes containing a CN-substituted all-carbon quaternary center. Experimental and theoretical studies revealed that the reaction likely involves a Michael/aldol/rearrangement sequence in a domino manner.

Graphical abstract: Cascade Michael/aldol/rearrangement between phenacylmalononitriles and maleimides: highly diastereoselective access to functionalized bicyclic cyclopentenes containing a CN-substituted all-carbon quaternary center
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