Subscribe to RSS
DOI: 10.1055/a-2352-7116
The Addition of Alkylation alfa-Hydroxy-benzylphosphonates to Dialkyl Acetylenedicarboxylates; Catalytic Hydrogenation of the Adducts
Supported by: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal K134318alfa-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.
Publication History
Received: 24 May 2024
Accepted after revision: 25 June 2024
Accepted Manuscript online:
25 June 2024
© . Thieme. All rights reserved.
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany