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

被引：0

作者：

Milen, Matyas ^{[1
,2
]}

Bese, Cintia ^{[1
]}

Kovacs, Csenge ^{[1
]}

Dancso, Andras ^{[2
]}

Keglevich, Gyorgy ^{[1
]}

机构：

[1] Budapest Univ Technol & Econ, Fac Chem Technol & Biotechnol, Dept Organ Chem & Technol, Muegyet Rkp 3, H-1111 Budapest, Hungary

[2] Egis Pharmaceut Plc, Chem Res Div, POB 100, H-1475 Budapest, Hungary

来源：

SYNTHESIS-STUTTGART | 2024年 / 56卷 / 19期

关键词：

addition; alkenation; alkylation; hydrogenation; phosphates; HIGH-YIELDING PREPARATION; SOLVENT-FREE SYNTHESIS; HERBICIDAL ACTIVITIES; BIOLOGICAL-ACTIVITY; HYDROXYPHOSPHONATES; DERIVATIVES; AMINOPHOSPHONATES; INHIBITORS; EFFICIENT;

D O I：

10.1055/a-2352-7116

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-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.

引用

页码：3074 / 3082

页数：9

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