Catalytic asymmetric dearomative [4+2] annulation of 2-nitrobenzofurans and 5H-thiazol-4-ones: stereoselective construction of dihydrobenzofuran-bridged polycyclic skeletons
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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2-硝基苯并呋喃和5H-噻唑-4-酮的催化不对称脱芳香[4 2]环化：二氢苯并呋喃桥联多环骨架的立体选择性构建
DOI：
10.1039/d1qo01061a
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发表时间：
2021
影响因子：
5.4
通讯作者：
Weicheng Yuan
中科院分区：
文献类型：
--
作者：
Jian-Qiang Zhao;Shun Zhou;Zhen-Hua Wang;Yong You;Shuang Chen;Xiong-Li Liu;Ming-Qiang Zhou;Weicheng Yuan
首次描述了2-硝基苯并呋喃和5H-噻唑-4-酮的有机催化不对称脱芳香[4 + 2]环化反应。以手性二肽方酰胺为催化剂，在温和条件下得到了一系列具有四个连续立构中心（包括三个四级立构中心）的二氢苯并呋喃桥联多环化合物，具有优异的非对映选择性和高对映选择性。初步生物学评价表明，该产品对人类癌细胞系A549和K562表现出令人印象深刻的细胞毒性。
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.