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Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: synthesis of highly substituted chiral spirodihydrocoumarins†‡
Dhevalapally B. Ramachary,R. Madhavachary,M. Shiva Prasad
Organic & Biomolecular Chemistry Pub Date : 02/10/2012 00:00:00 , DOI:10.1039/C2OB07122C
Abstract

A general approach to asymmetric synthesis of highly substituted spirodihydrocoumarins with a quaternary stereocenter was achieved through neighboring ortho-hydroxyl group induced sequential Michael–lactonization reactions on 2-(2-nitrovinyl)phenols with alkyl cyclopentanone-2-carboxylates in the presence of a catalytic amount of quinineNH–thiourea followed by p-TSA.

Graphical abstract: Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: synthesis of highly substituted chiral spirodihydrocoumarins
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