Reaction of cyclic. alpha.-hydroxy epoxides with a strong base: a new 1, 2-rearrangement, evidence for a carbenoid pathway.

E Doris, L Dechoux, C Mioskowski

Index: Doris, Eric; Dechoux, Luc; Mioskowski, Charles Journal of the American Chemical Society, 1995 , vol. 117, # 51 p. 12700 - 12704

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Citation Number: 35

Abstract

Abstract: Several substituted five-and six-membered cyclic a,,!?-unsaturated ketones are readily available by treatment of the corresponding a-hydroxy epoxides with an organolithium reagent. The reaction involves a new carbenoid 1, 2-alkyl rearrangement. Evidence for the carbenoid intermediate has been obtained by an intramolecular trapping of the highly reactive species.

Regio-and Stereoselective Cyclopentannulation with Ketones and Propargyl Alcohol Derivatives. Synthesis of dl-Nootkatone and dl-Muscopyridine

[Hiyama, Tamejiro; Shinoda, Masaki; Saimoto, Hiroyuki; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 9 p. 2747 - 2758]

Cyclopentenone synthesis from 1, 1-dichloroallyllithium-ketone adducts as well as from dichlorocarbene-allyl alcohol adducts.

[Hiyama, Tamejiro; Shinoda, Masaki; Tsukanaka, Masao; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 4 p. 1010 - 1014]