Synthesis of Non-Racemic 1-Hydroxy Cycloalkenecarboxylic Acids by Metathesis of Dialkylated Glycolate Derivatives.

Liliana Rapado; Vajira Bulugahapitiya; Philippe Renaud

doi:10.3390/ecsoc-3-01729

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Site and Stereoselectivities in the High Pressure Reactionof Furan with Dimethyl 7-isopropylidenebicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate and Tetramethyl7-isopropylidenebicyclo[2.2.1]hepta-2,5-diene-2,3,5,6-tetracarboxylate.

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Synthesis of Heterocycles Using Tandem Cyclization Processes.

Synthesis of Non-Racemic 1-Hydroxy Cycloalkenecarboxylic Acids by Metathesis of Dialkylated Glycolate Derivatives.

Liliana Parra Rapado

Vajira Bulugahapitiya

Philippe Renaud

¹ Université de Fribourg, Institut de Chimie Organique, Pérolles, CH-1700 Fribourg, Switzerland

Published: 01 November 1999 by MDPI in The 3rd International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-3-01729

Abstract: A particularly flexible general way to synthesize 1-hydroxy cycloalkenecarboxylic acid derivatives from 2-tert-butyl-2-methyl-1,3-dioxolan-5-one, a chiral equivalent of glycolic acid, is reported. The method is based on a double enolate alkylation of the glycolate derivative followed by ring closing metathesis. A formal synthesis of (-)-quinic acid is reported to demonstate the potential of this approach

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Liliana Rapado

Vajira Bulugahapitiya

Philippe Renaud