通过铜（II）/SPDO催化2,3-二氢呋喃与醌酯的[3+2]环加成反应实现2,3,3a,8a-四氢呋喃并[2,3-]苯并呋喃骨架的对映选择性合成。
Enantioselective Synthesis of 2,3,3a,8a-Tetrahydrofuro[2,3-]benzofuran Scaffolds Enabled by Cu(II)/SPDO-Catalyzed [3+2] Cycloaddition of 2,3-Dihydrofuran and Quinone Esters.
作者信息
Zhu Jin-Xin, Tian Jin-Miao, Chen Yao-Yao, Hu Xue-Jiao, Han Xue, Chen Wenchao, Yang Zhikun, Bao Xiaoze, Ye Xinyi, Chen Hua, Zhang Fu-Min, Wang Hong, Tu Yong-Qiang
机构信息
College of Pharmaceutical Science and Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
出版信息
J Org Chem. 2023 Oct 20;88(20):14670-14675. doi: 10.1021/acs.joc.3c01681. Epub 2023 Oct 10.
An asymmetric [3+2] cycloaddition of quinone esters with 2,3-dihydrofuran has been realized via a newly developed Cu(II)/SPDO complex. It provides straightforward access to 2,3,3a,8a-tetrahydrofuro[2,3-]benzofurans (TFB) with high enantioselectivity (up to 97.5:2.5 er) and diastereoselectivity (all >20:1 dr). The resulting adducts contain two adjacent stereocenters and a continuously functionalized benzene ring. Additionally, this transformation could be easily performed on a gram scale, allowing for expedient synthesis of natural dihydroaflatoxin D and aflatoxin B.
通过新开发的铜（II）/SPDO配合物实现了醌酯与2,3-二氢呋喃的不对称[3+2]环加成反应。该反应能直接得到对映选择性高（对映体比例高达97.5:2.5）和非对映选择性高（所有非对映体比例均>20:1）的2,3,3a,8a-四氢呋喃并[2,3-]苯并呋喃（TFB）。所得加合物含有两个相邻的立体中心和一个连续官能化的苯环。此外，这种转化可以很容易地在克级规模上进行，便于快速合成天然二氢黄曲霉毒素D和黄曲霉毒素B。
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