290306-18-2Relevant academic research and scientific papers
Synthesis of non-racemic 1-hydroxycycloalkene-1-carboxylic-acid derivatives by metathesis of α,α-dialkylated glycolate derivatives
Rapado, Liliana Parra,Bulugahapitiya, Vajira,Renaud, Philippe
, p. 1625 - 1632 (2000)
A particularly flexible general way to synthesize 1-hydroxycycloalkene- 1-carboxylic-acid derivatives from 2-(tert-butyl)-2-methyl-1,3-dioxolan-4-one (1), 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 demonstrate the potential of this approach.
Catalytic enantioselective alkylation of substituted dioxanone enol ethers: ready access to C(α)-tetrasubstituted hydroxyketones, acids,and esters
Seto, Masaki,Roizen, Jennifer L.,Stoltz, Brian M.
supporting information; experimental part, p. 6873 - 6876 (2009/04/06)
(Chemical Equation Presented) Adaptive Alkylation: Palladium-catalyzed asymmetric alkylation enables access to fully substituted enantioenriched oxygenated stereocenters, which can be transformed easily to α-hydroxyketones, esters, and acids, providing a catalytic, enantioselective synthesis for natural products.
