Issue 30, 2012

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

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

Supplementary files

Article information

Article type
Communication
Submitted
18 dek 2011
Accepted
10 fev 2012
First published
10 fev 2012

Org. Biomol. Chem., 2012,10, 5825-5829

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

D. B. Ramachary, R. Madhavachary and M. S. Prasad, Org. Biomol. Chem., 2012, 10, 5825 DOI: 10.1039/C2OB07122C

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