[PDF][PDF] Synthesis of Non-Racemic 1-Hydroxycycloalkene-1-carboxylic-Acid Derivatives by Metathesis of a, a-Dialkylated Glycolate Derivatives
LP Rapado, V Bulugahapitiya, P Renaud… - Helvetica Chimica …, 2000 - academia.edu
Conclusions.±We have presented here an efficient synthesis of cyclic non-racemic 1-
hydroxycycloalkene-1-carboxylic-acid derivatives. The absolute configuration at C (1) can
be preestablished by the choice of the starting enantiomer of 1 or by the sequence of the
alkylations. This approach is particularly flexible and should be applicable to a wide range of
biologically relevant compounds.
hydroxycycloalkene-1-carboxylic-acid derivatives. The absolute configuration at C (1) can
be preestablished by the choice of the starting enantiomer of 1 or by the sequence of the
alkylations. This approach is particularly flexible and should be applicable to a wide range of
biologically relevant compounds.
Synthesis of Non‐Racemic 1‐Hydroxycycloalkene‐1‐carboxylic‐Acid Derivatives by Metathesis of α,α‐Dialkylated Glycolate Derivatives
L Parra Rapado, V Bulugahapitiya… - Helvetica Chimica …, 2000 - Wiley Online Library
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.
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.
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