127915-54-2Relevant academic research and scientific papers
Selective Palladium-Catalyzed Allenic C?H Bond Oxidation for the Synthesis of [3]Dendralenes
Qiu, Youai,Posevins, Daniels,B?ckvall, Jan-E.
, p. 13112 - 13116 (2017)
A highly selective palladium-catalyzed allenic C?H bond oxidation was developed, and it provides a novel and straightforward synthesis of [3]dendralene derivatives. A variety of [3]dendralenes with diverse substitution patterns are accessible with good efficiency and high stereoselectivity. The reaction tolerates a broad substrate scope containing various functional groups on the allene moiety, including ketone, aldehyde, ester, and phenyl groups. Also, a wide range of olefins with both electron-donating and electron-withdrawing aryls, acrylate, sulfone, and phosphonate groups are tolerated.
1,6-reduction of 2-en-4-ynoates using lithium di-s-butylcyanocuprete
Krause, Norbert,Handke, Gabriele
, p. 7229 - 7232 (2007/10/02)
Treatment of 2-en-4-ynotes 1 with lithium di-s-butylcyanocuprate in diethyl ether yields the 1,6-reduction products 2, whereas in tetrahydrofuran the 1,6-addition products 4 are obtained.
Synthesis of Allenes by 1,6-Addition of Organocuprates to Polarized Enynes
Krause, Norbert
, p. 2173 - 2180 (2007/10/02)
Ten β-allenic esters, ketones, and thioesters 15 bearing alkyl, alkenyl, aryl, and trimethylsilyl groups are synthesized in 57-85percent yield by 1,6-addition of organocuprates to polarized enynes 10.The dependence of the regioselectivity of the protonation of the allenyl enolate intermediate 7 on the protonating agent is studied; pure allenes are obtained by quenching the intermediate with pivalic acid at -80 deg C.The method is applied in a short synthesis of pseudoionone (18).
