Synthesis of 1,3-Bis(diphenylphosphinoyl)alkanes via Double Addition of Diphenylphosphine to α,β-Unsaturated Carbonyl Compounds: Sequential 1,4- and 1,2-Addition Promoted by NbCl 5 -BF 3 ·OEt

Takeshi Hashimoto, Hideki Maeta, Takashi Matsumoto, Mitsuo Morooka, Shigeru Ohba, Keisuke Suzuki

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12 Citations (Scopus)

Abstract

Lewis acid-promoted double addition of diphenylphosphine to various α,β-unsaturated aldehydes and ketones is described. By utilizing niobium(V) chloride and diethyl etherboron trifluoride complex (stoichiometric), the reaction provides the monooxides of 1,3-bis(diphenylphosphino)alkane, which were oxidatively worked up to yield the corresponding bisoxides 1-6 in high yields. The reaction of diphenylphosphine with 2-cyclohexenone afforded trans-1,3-bis(diphenylphosphinoyl)-cyclohexane (6) as the sole isolable product. The relative stereochemistry of 6 was rigorously determined by X-ray crystallography.

Original languageEnglish
Pages (from-to)340-342
Number of pages3
JournalSynlett
Volume1992
Issue number4
DOIs
Publication statusPublished - 1992 Apr

ASJC Scopus subject areas

  • Organic Chemistry

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