Journal of Organic Chemistry p. 2343 - 2351 (1986)
Update date:2022-08-03
Topics:
Wenkert, Ernest
Angell, E. Charles
Ferreira, Vitor F.
Michelotti, Enrique L.
Piettre, Serge R.
et al.
Interaction of magnesium indolates and allyl oxides in the presence of bis(triphenylphosphine)nickel dichloride results in indole β-allylation, except in cases involving highly substituted indoles and allyl alcohols.This method permits the β-prenylation of indole and α-prenylation of ketones (by way of their magnesium enaminates).Base-induced interaction of ethynyldimethylcarbinyl chloride and indole under a variety of conditions yields β-(β,β-dimethylvinyl)quinoline as well as variously dehydroprenylated indoles. α-Lithiation of N-(benzenesulfonyl)indole followed by treatmentwith prenyl bromide or β,β-dimethylacrylyl chloride produces α-prenyl- or α-oxoprenylidole derivatives, the sodium amalgam reduction of the former of which yields α-prenylidole.Interaction of β-cuprated N-(benzenesulfonyl)indole with the same halides followed by reduction affords β-prenylindole and β-oxoprenylindole, the latter also being the product of the reaction of magnesium indolate and the acid chloride.Lithium aluminum hydride reduction of 1-(benzenesulfonyl)-3-oxoprenylindole affords an alcohol, whose base hydrolysis produces β-dehydroprenylindole, a compound whose dimerization has led previously to naturally occuring yuehchukene.
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