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ChemInform Abstract: Synthesis of 3-Oxoalkylphosphonates via the Conjugate Addition of Acylcuprates to Diethyl Vinylphosphonate.

✍ Scribed by Nan-Sheng Li; Su Yu; George W. Kabalka

Publisher: John Wiley and Sons
Year: 2010
Weight: 30 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199934196

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✦ Synopsis

Synthesis of 3-Oxoalkylphosphonates via the Conjugate Addition of Acylcuprates to Diethyl Vinylphosphonate.

-Acylcuprates, generated in situ from dialkylcyanocuprates (I) and carbon monoxide, are added to vinylphosphonate (III) to give, after hydrolysis, phosphonates (IV) in good yields. Phosphonates (IVb) and (IVc) are also obtained from monoalkylcyanocuprates by the same route but in lower yields. The butyl derivative (IVa) is not formed by the latter reaction. Allylic derivatives (VI) are synthesized in good yields by trapping of the reaction intermediate with allylic bromides (V).

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