The Addition of α-Hydroxy-benzylphosphonates to Dialkyl Acetyl­enedicarboxylates; Catalytic Hydrogenation of the Adducts

Abstract

α-Hydroxy-benzylphosphonates obtained by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites were added to the triple bond of dialkyl acetylenedicarboxylates. Optimum conditions involved a 24 hours stirring in the presence of 10% diazabicycloundecene in dichloromethane to afford the adducts as a mixture of predominant E- and a minor Z-isomers in 75–90% yields after flash chromatography. The structures of the geometrical isomers were confirmed by NOE- and ROE-measurements. Catalytic hydrogenation of the olefinic moiety of the adducts led to the diastereoisomers of corresponding saturated derivatives.

Key words

addition - alkenation - alkylation - hydrogenation - phosphates

Publikationsverlauf

Eingereicht: 24. Mai 2024

Angenommen nach Revision: 25. Juni 2024

Accepted Manuscript online:
25. Juni 2024

Artikel online veröffentlicht:
18. Juli 2024

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