4746-09-2Relevant articles and documents
Diastereoselective and Stereodivergent Synthesis of 2-Cinnamylpyrrolines Enabled by Photoredox-Catalyzed Iminoalkenylation of Alkenes
Shen, Xu,Huang, Congcong,Yuan, Xiang-Ai,Yu, Shouyun
, p. 9672 - 9679 (2021/03/16)
A photoredox-catalyzed iminoalkenylation of γ-alkenyl O-acyl oximes has been developed. Readily available alkenylboronic acids serve as alkenylation reagents, leading to densely functionalized pyrrolines. Both (E)- and (Z)-cinnamylpyrrolines are accessible depending on the reaction solvent. In dichloromethane, (E)-cinnamylpyrrolines are produced through a photoredox-mediated single-electron-transfer process. In tetrahydrofuran, (Z)-cinnamylpyrrolines are generated by photocatalytic contra-thermodynamic E-to-Z isomerization of (E)-cinnamylpyrrolines though an energy-transfer pathway. Two stereocenters are established with complete diastereoselectivity and only one diastereomer is isolated.
Catalyst-free chemoselective conjugate addition and reduction of α,β-unsaturated carbonyl compounds: Via a controllable boration/protodeboronation cascade pathway
Huang, Xi,Hu, Junjie,Wu, Mengying,Wang, Jiayi,Peng, Yanqing,Song, Gonghua
, p. 255 - 260 (2018/01/12)
A novel, efficient transition-metal-free and controllable boration/protodeboronation strategy has been developed for the chemoselective conjugate addition and 1,4-reduction of α,β-unsaturated carbonyl compounds. Without any metal-catalyst or base, a series of β-boration products of α,β-unsaturated carbonyl compounds was easily obtained in moderate to excellent yields in a mixed solvent of ethanol and water. The presence of a catalytic amount of Cs2CO3 can effectively induce further protodeboronation reaction towards 1,4-reduction products at higher reaction temperature. Therefore, by slightly changing the reaction conditions, the boration or reduction products of α,β-unsaturated carbonyl compounds can be controllably obtained. Mechanistic studies revealed that Cs2CO3 played the key role in activating the protodeboronation step. This transition-metal-catalyst-free and product controllable method provides a useful and eco-friendly tool for the highly chemoselective preparation of the β-boration products and 1,4-reduction products of α,β-unsaturated carbonyl compounds.
Iridium-catalyzed regioselective decarboxylative allylation of β-ketoacids: Efficient construction of γ,δ-unsaturated ketones
Chen, Shu-Jie,Lu, Guo-Ping,Cai, Chun
supporting information, p. 11512 - 11514 (2016/01/15)
A highly regioselective protocol for the direct synthesis of γ,δ-unsaturated ketones from β-ketoacids and allylic alcohols was proposed and accomplished relying on the combination of [Ir(cod)Cl]2 and 10-camphorsulfonic acid via decarboxylative allylation.
