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Synthesis 2024; 56(19): 3074-3082
DOI: 10.1055/a-2352-7116
DOI: 10.1055/a-2352-7116
paper
The Addition of α-Hydroxy-benzylphosphonates to Dialkyl Acetylenedicarboxylates; Catalytic Hydrogenation of the Adducts
Authors
This project was supported by the National Research, Development and Innovation Office, Hungary (K134318).
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2352-7116.
- Supporting Information (PDF)
Publication History
Received: 24 May 2024
Accepted after revision: 25 June 2024
Accepted Manuscript online:
25 June 2024
Article published online:
18 July 2024
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