铑
恶唑啉
平面手性
化学
二烯
手性(物理)
配体(生物化学)
立体化学
立体中心
催化作用
对映选择合成
药物化学
组合化学
有机化学
物理
受体
生物化学
天然橡胶
手征对称破缺
量子力学
夸克
Nambu–Jona Lasinio模型
作者
Nikita M. Ankudinov,Yulia V. Nelyubina,Dmitry S. Perekalin
标识
DOI:10.1002/chem.202200195
摘要
Diene rhodium complexes are important catalysts in modern organic synthesis. Herein, we report a new approach to such complexes with the uncommon planar chirality. The synthesis is achieved by face-selective coordination of the prochiral 2,5-disubstituted-1,4-benzoquinones (R2 -Q) with rhodium precursors containing the chiral auxiliary ligand S-salicyl-oxazoline (S-Salox). Such coordination leads to the formation of (R,R-R2 -Q)Rh(S-Salox) complexes in high yields and with exceptional diastereoselectivity (d. r.>20 : 1). Subsequent replacement of the auxiliary ligand provides various benzoquinone rhodium complexes with retention of the planar chirality. Combined theoretical and experimental studies show that due to their electron-withdrawing nature benzoquinones bind metals stronger than the related 1,4-cyclohexadiene, but weaker than other common diene ligands, such as cyclooctadiene.
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