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Synthesis 1995; 1995(7): 769-771
DOI: 10.1055/s-1995-4000
short paper
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A Convenient Stereoselective Synthesis of 1,3-Dienylphosphonates and 1-En-3-ynylphosphonates and Their Phosphine Oxide Analogs

Xiaoling Huang, Chunming Zhang, Xiyan Lu*
  • *Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People’s Republic of China, Fax +86(21)4166128
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Publikationsdatum:
31. Dezember 2000 (online)

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Ethynylphosphonates (or phosphine oxides) react with a lithium halide in acetic acid at 70°C to yield (Z)-2-halovinylphosphonates (or phosphine oxides), which give (1Z,3E)-dienylphosphonates and (1Z)-en-3-ynylphosphonates (phosphine oxides) after coupling with alkenes and alkynes, respectively, in the presence of a palladium catalyst.

stereoselective hydrohalogenation - ethynylphosphonates - 1,3-dienylphosphonates - 1-en-3-ynylphosphonates - phosphine oxides