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

Ramachary, Dhevalapally B. ; Madhavachary, R. ; Prasad, M. Shiva (2012) Observation of neighboring ortho-hydroxyl group participation in organocatalytic asymmetric sequential Michael-lactonization reactions: synthesis of highly substituted chiral spirodihydrocoumarins Organic and Biomolecular Chemistry, 10 (30). p. 5825. ISSN 1477-0520

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Official URL: http://doi.org/10.1039/C2OB07122C

Related URL: http://dx.doi.org/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 quinine–NH–thiourea followed by p-TSA.

Item Type:Article
Source:Copyright of this article belongs to The Royal Society of Chemistry.
ID Code:120678
Deposited On:03 Jul 2021 08:08
Last Modified:03 Jul 2021 08:08

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