20937-29-5Relevant academic research and scientific papers
Enabling the development of N-Heterocyclic Carbene (NHC) catalyzed reactions: Practical methods for the preparation of 1-acyl-2-alkylcycloalkenes from cycloalkanones
Ryan, Sarah J.,Candish, Lisa,Martinez, Ivn,Lupton, David W.
, p. 1148 - 1157 (2011/11/06)
The synthesis of 1-acyl-2-alkylcycloalkenes from a variety of cycloalkanones has been achieved via either-keto enol phosphates or-bromoenones. Both methods exploit simple and readily scalable transformations allowing the preparation of the desired compoun
N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition/decarboxylation of silyl dienol ethers with α,β-unsaturated acid fluorides
Ryan, Sarah J.,Candish, Lisa,Lupton, David W.
, p. 4694 - 4697 (2011/05/28)
Herein we report the first all-carbon N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition. The reaction proceeds with α,β-unsaturated acid fluorides and silyl dienol ethers and produces 1,3-cyclohexadienes with complete diastereocontrol (dr >20:1) while demonstrating a new type of reaction cascade exploiting α,β-unsaturated acyl azoliums.
Novel Acylation of Aliphatic Olefins Promoted by Active Zinc Compounds
Shono, Tatsuya,Nishiguchi, Ikuzo,Sasaki, Manji,Ikeda, Haruhiko,Kurita, Makoto
, p. 2503 - 2505 (2007/10/02)
It was found that acylation of a variety of aliphatic olefins with acid chlorides is efficiently promoted by active zinc compounds, which were prepared from a Zn/Cu couple and alkyl iodides.The crude product mixtures were subsequently treated with 1 M KOH in methanol or were subjected to catalytic hydrogenation to afford the corresponding α,β-unsaturated or saturated ketones in good to moderate yields.It was also shown that the reaction fully follows the Markovnikov rule.
