127915-55-3Relevant academic research and scientific papers
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).
