Catalytic asymmetric dearomative [4 + 2] annulation of 2-nitrobenzofurans and 5H-thiazol-4-ones: stereoselective construction of dihydrobenzofuran-bridged polycyclic skeletons

文献情報

出版日 2021-09-16

DOI 10.1039/D1QO01061A

インパクトファクター 5.281

著者

Jian-Qiang Zhao, Zhen-Hua Wang, Yong You, Shuang Chen, Xiong-Li Liu, Ming-Qiang Zhou, Wei-Cheng Yuan

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要旨

An organocatalytic asymmetric dearomative [4 + 2] annulation of 2-nitrobenzofurans and 5H-thiazol-4-ones is described for the first time. With a chiral dipeptide-based squaramide as the catalyst, a series of dihydrobenzofuran-bridged polycyclic compounds bearing four contiguous stereocenters including three quaternary stereogenic centers were obtained with excellent diastereoselectivities and high enantioselectivities under mild conditions. Preliminary biological evaluation indicated that the products exhibit impressive cytotoxicity against the human cancer cell lines A549 and K562.

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

Catalytic asymmetric dearomative [4 + 2] annulation of 2-nitrobenzofurans and 5H-thiazol-4-ones: stereoselective construction of dihydrobenzofuran-bridged polycyclic skeletons

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