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Synlett 1992; 1992(4): 340-342
DOI: 10.1055/s-1992-22007
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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 NbCl5-BF3·OEt2

Takeshi Hashimoto* , Hideki Maeta, Takashi Matsumoto, Mitsuo Morooka, Shigeru Ohba, Keisuke Suzuki
  • *Department of Chemistry, Keio University, Hiyoshi, Yokohama 223, Japan
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Publication Date:
08 March 2002 (online)

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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.

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