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Synthesis
DOI: 10.1055/a-2352-7116
paper

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

Mátyás Milen 
1   Synthetic, Egis Pharmaceuticals, Budapest, Hungary
,
Cintia Bese
2   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary (Ringgold ID: RIN61810)
,
Csenge Kovács
2   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary (Ringgold ID: RIN61810)
,
András Dancsó
3   Structure Proving, Egis Pharmaceuticals, Budapest, Hungary
,
György Keglevich
4   Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
› InstitutsangabenGefördert durch: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal K134318
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alfa-Hydroxy-benzylphosphonates obtained by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites were added on the triple bond of dialkyl acetylenedicarboxylates. Optimum conditions involved a 24 h’ stirring in the presence of 10% of diazabicycloundecene in dichloromethane to afford the adducts as a mixture of predominant “E” and a minor “Z” izomers in 75–90% yields after flash chromatography. Structure of the geometrical isomers was confirmed by NOE- and ROE measurements. Catalytic hydrogenation of the olefinic moiety of the adducts led to the diastereomers of corresponding saturated derivatives.



Publikationsverlauf

Eingereicht: 24. Mai 2024

Angenommen nach Revision: 25. Juni 2024

Accepted Manuscript online:
25. Juni 2024

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