1241973-04-5Relevant academic research and scientific papers
Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazine nucleophiles
Yang, Wen,Luo, Renshi,Yang, Dingqiao
, p. 21103 - 21124 (2016/01/25)
Iridium-catalyzed asymmetric ring-opening of oxabenzonorbornadienes with N-substituted piperazines was described. The reaction afforded the corresponding ring-opening products in high yields and moderate enantioselectivities in the presence of 2.5 mol % [Ir(COD)Cl]2 and 5.0 mol % (S)-p-Tol-BINAP. The effects of various chiral bidentate ligands, catalyst loading, solvent, and temperature on the yield and enantioselectivity were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding trans-ring opened products based on the X-ray structure of product 2i.
Highly efficient rhodium-catalyzed asymmetric ring-opening reactions of oxabenzonorbornadiene with amine nucleophiles
Long, Yuhua,Zhao, Shuangqi,Zeng, Heping,Yang, Dingqiao
experimental part, p. 124 - 133 (2010/11/05)
Rhodium-catalyzed asymmetric ring-opening reactions of oxabenzonorbornadienes with aliphatic primary amines and substituted N-phenylpiperazines were investigated. These reactions are featured with the formation of a new carbon-nitrogen bond via an intermolecular allylic displacement of the bridgehead oxygen with amine nucleophiles, which offered the corresponding products in good to excellent yields (up to 97%) with excellent enantioselectivities (up to 99%ee). Graphical Abstract: Rhodium-catalyzed asymmetric ring-opening reactions of oxabenzonorbornadienes with aliphatic primary amines and substituted N-phenylpiperazines were investigated. These reactions are featured with the formation of a new carbon-nitrogen bond via an intermolecular allylic displacement of the bridgehead oxygen with amine nucleophiles, which offered the corresponding products in good to excellent yields (up to 97%) with excellent enantioselectivities (up to 99 %ee).
