The highly basic and poorly nucleophilic phosphazene base P-1-t-Bu promotes the Darzens condensation of alpha-halo esters with aromatic aldehydes affording alpha,beta-epoxy esters in nearly quantitative yields under mild conditions and in short reaction times. The more basic P-4-t-Bu phosphazene was found useful with low reactivity aldehydes. These reactions can be performed in aprotic organic solvents of low polarity, thus minimizing the hydrolysis of alpha,beta-epoxy esters which often accompanies the base-promoted Darzens condensations.

Highly Efficient Darzens Reactions Mediated by Phosphazene Bases under Mild Conditions

Lops, Carmine;Pengo, Paolo
;
Pasquato, Lucia
2022-01-01

Abstract

The highly basic and poorly nucleophilic phosphazene base P-1-t-Bu promotes the Darzens condensation of alpha-halo esters with aromatic aldehydes affording alpha,beta-epoxy esters in nearly quantitative yields under mild conditions and in short reaction times. The more basic P-4-t-Bu phosphazene was found useful with low reactivity aldehydes. These reactions can be performed in aprotic organic solvents of low polarity, thus minimizing the hydrolysis of alpha,beta-epoxy esters which often accompanies the base-promoted Darzens condensations.
2022
Pubblicato
https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/open.202200179
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11368/3040074
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