31552-04-2Relevant articles and documents
Palladium-Catalyzed Modular and Enantioselective cis-Difunctionalization of 1,3-Enynes with Imines and Boronic Reagents
He, Qing,Zhu, Lei,Yang, Zhen-Hong,Zhu, Bo,Ouyang, Qin,Du, Wei,Chen, Ying-Chun
supporting information, p. 17989 - 17994 (2021/11/10)
Here we report that a palladium(0) complex can mediate the unprecedented intermolecular coupling reaction of 1,3-enynes and N-sulfonylimines regio- and stereoselectively, and the resultant palladium(II) species undergo a cascade Suzuki reaction with organ
Regioselective Access to 3-Ethylideneflavanones via Rhodium(I)-Catalyzed 1,3-Enyne Hydroacylation/Annulation Cascades
Chang, Zhi-Xin,Li, Fu-Rong,Xia, Chengcai,Li, Fei,Li, Hong-Shuang
supporting information, p. 1722 - 1726 (2021/02/20)
The highly efficient synthesis of 3-ethylideneflavanones through sequential rhodium(I)-catalyzed hydroacylation of terminal aryl-substituted 1,3-enynes with chelating aldehydes and annulation is described. This straightforward protocol highlights an unprecedented C3-regioselective hydroacylation of 1,3-enynes, excellent functional group compatibility, and complete atom economy. (Figure presented.).
Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design
Adamson, Nathan J.,Jeddi, Haleh,Malcolmson, Steven J.
supporting information, p. 8574 - 8583 (2019/06/04)
In this study, we establish that conjugated enynes undergo selective 1,4-hydroamination under Pd catalysis to deliver chiral allenes with pendant allylic amines. Several primary and secondary aliphatic and aryl-substituted amines couple with a wide range of mono- and disubstituted enynes in a nonenantioselective reaction where DPEphos serves as the ligand for Pd. Benzophenone imine acts as an ammonia surrogate to afford primary amines in a two-step/one-pot process. Examination of chiral catalysts revealed a high degree of reversibility in the C-N bond formation that negatively impacted enantioselectivity. Consequently, an electron-poor ferrocenyl-PHOX ligand was developed to enable efficient and enantioselective enyne hydroamination.