Bulletin of the Chemical Society of Japan p. 2456 - 2464 (1992)
Update date:2022-08-04
Topics:
Wada, Eiji
Funakoshi, Junji
Kanemasa, Shuji
The reactions of 2-oxo-3-alkenylphosphonates with carbonyl-stabilized carbanions directly lead to 2-cyclohexen-1-ones through a sequence of Michael reaction and intramolecular Horner-Emmons olefination.On the other hand, the Lewis acid-mediated reactions with silyl enol ethers produce 1,5-diketones as Michael adducts, which then undergo cyclization on treatment with sodium hydride or triethylamine/zinc (II) bromide to afford 2-cyclohexen-1-ones or 2-phosphinyl-2-cyclohexen-1-ones, respectively.
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