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Synthesis of Non‐Racemic 1‐Hydroxycycloalkene‐1‐carboxylic‐Acid Derivatives by Metathesis of α , α ‐Dialkylated Glycolate Derivatives
Author(s) -
Parra Rapado Liliana,
Bulugahapitiya Vajira,
Renaud Philippe
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000705)83:7<1625::aid-hlca1625>3.0.co;2-w
Subject(s) - chemistry , glycolic acid , metathesis , carboxylic acid , quinic acid , alkylation , derivative (finance) , ring closing metathesis , organic chemistry , combinatorial chemistry , catalysis , lactic acid , genetics , bacteria , financial economics , economics , polymerization , biology , polymer
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.