Iridium-catalyzed intramolecular asymmetric allylic etherification of salicylic acid derivatives with chiral-bridged biphenyl phosphoramidite ligands

文献情報

出版日 2021-06-11

DOI 10.1039/D1QO00566A

インパクトファクター 5.281

著者

Bendu Pan, Jia-Sheng Ouyang, Yaqi Zhang, Hao Liang, Qiang Ni, Bin Chen, Xiaoyun Pu, Long Jiang, Rihui Cao, Liqin Qiu

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要旨

Iridium-catalyzed intramolecular asymmetric allylic etherification of salicylic acid derivatives was successfully realized for the first time. By using chiral-bridged biphenyl phosphoramidite ligand L7, a class of novel chiral 1,4-benzoxazepinones was prepared conveniently with good to excellent yields (up to 99%) and high enantioselectivities (up to 99% ee). The effect of different substituents on the enantioselectivity was also discussed. Compared with BINOL or biphenol-derived counterparts, catalysis with ligand L7 has obvious advantages in terms of catalytic activity and enantioselectivity. Mild conditions and a wide substrate scope demonstrate the practicability of this method. It was also found that the configuration of the product was directly related to the configuration of the alkene substrate and the E-substrate is more suitable for this reaction to obtain better enantioselectivity.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry