105575-96-0Relevant academic research and scientific papers
Synthesis of Cyclopentenones with Reverse Pauson-Khand Regiocontrol via Ni-Catalyzed C-C Activation of Cyclopropanone
Jang, Yujin,Lindsay, Vincent N. G.
supporting information, p. 8872 - 8876 (2020/12/02)
A formal [3 + 2] cycloaddition between cyclopropanone and alkynes via Ni-catalyzed C-C bond activation has been developed, where 1-sulfonylcyclopropanols are employed as key precursors of cyclopropanone in the presence of trimethylaluminum. The transformation provides access to 2,3-disubstituted cyclopentenones with complete regiocontrol, favoring reverse Pauson-Khand products, where the large substituent is located at the 3-position of the ring. In the process, the trimethylaluminum additive is thought to play multiple roles, including as a Br?nsted base triggering the equilibration to cyclopropanone and liberation of methane, as well as a source of Lewis acid to activate the carbonyl group toward Ni-catalyzed C-C activation.
A NOVEL SYNTHESIS OF CYCLOPENTENONES AND CYCLOHEXENONES VIA CYCLIACYLATION OF LITHIOALKENYLCARBOXAMIDES
Sawada, Hiroyuki,Webb, Michael,Stoll, A. Timothy,Negishi, Ei-ichi
, p. 775 - 778 (2007/10/02)
The reaction of 1-iodo-3-bromopropene derivatives (1) with lithium enolates of N,N-dialkylcarboxamides followed by treatment of the allylation product (2) with two equiv of t-BuLi cleanly provides cyclopentenones in high yields, while the corresponding cycliacylation reaction of 6-iodo-5-hexenamides provides cyclohexenones.
