Diastereoselective and Enantioselective Synthesis of α-p-Methoxyphenoxy-β-Lactones: Dependence on the Stereoelectronic Properties of the β-Hydroxy-α-p-Methoxyphenoxycarboxylic Acid Precursors
Abstract:Treatment of β-hydroxy-α-p-methoxyphenoxy
carboxylic acids derived from the asymmetric glycolate aldol addition
reaction with p-nitrobenzenesulfonyl chloride yielded
divergent results depending on the nature of the β-substituent
of the carboxylic acid. Substrates bearing either alkyl substituents
(R = -n-butyl, -n-octyl, -benzyl,
isopropyl, -tert-butyl) or aryl systems bearing electron-withdrawing
substituents (R = -p-C6H4Cl,
-p-C6H4Br, -p-C6H4NO2) yielded β-lactones.
In contrast, α-p-methoxyphenoxy-β-hydroxyc… Show more
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