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Enantioselective Synthesis of 2,3,3a,8a-Tetrahydrofuro[2,3-b]benzofuran Scaffolds Enabled by Cu(II)/SPDO-Catalyzed [3+2] Cycloaddition of 2,3-Dihydrofuran and Quinone Esters
Zhu, Jin-xin1,2; Tian, Jin-Miao1,2; Chen, Yao-Yao1,2; Hu, Xue-Jiao1,2; Han, Xue3,4; Chen, Wenchao1,2; Yang, Zhikun1,2; Bao, Xiaoze1,2; Ye, Xinyi1,2; Chen, Hua1,2; Zhang, Fu-Min3,4; Wang, Hong1,2; Tu, Yong-Qiang3,4
2023-10-10
Online publication date2023-10
Source PublicationJOURNAL OF ORGANIC CHEMISTRY   Impact Factor & Quartile
ISSN0022-3263 ; 1520-6904
EISSN1520-6904
Volume88Issue:20Pages:14670-14675
page numbers6
AbstractAn 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-b]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-2 and aflatoxin B-2.
PublisherAMER CHEMICAL SOC
DOI10.1021/acs.joc.3c01681
Indexed BySCIE ; IC
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:001082691900001
Original Document TypeArticle
PMID 37815481
Citation statistics
Document Type期刊论文
Identifierhttps://ir.lzu.edu.cn/handle/262010/569227
Collection兰州大学
Corresponding AuthorWang, Hong; Tu, Yong-Qiang
Affiliation
1.Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R China;
2.Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gre, Hangzhou 310014, Peoples R China;
3.Lanzhou Univ, State Key Lab Appl Organ Chem, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China;
4.Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China
Recommended Citation
GB/T 7714
Zhu, Jin-xin,Tian, Jin-Miao,Chen, Yao-Yao,et al. Enantioselective Synthesis of 2,3,3a,8a-Tetrahydrofuro[2,3-b]benzofuran Scaffolds Enabled by Cu(II)/SPDO-Catalyzed [3+2] Cycloaddition of 2,3-Dihydrofuran and Quinone Esters[J]. JOURNAL OF ORGANIC CHEMISTRY,2023,88(20):14670-14675.
APA Zhu, Jin-xin.,Tian, Jin-Miao.,Chen, Yao-Yao.,Hu, Xue-Jiao.,Han, Xue.,...&Tu, Yong-Qiang.(2023).Enantioselective Synthesis of 2,3,3a,8a-Tetrahydrofuro[2,3-b]benzofuran Scaffolds Enabled by Cu(II)/SPDO-Catalyzed [3+2] Cycloaddition of 2,3-Dihydrofuran and Quinone Esters.JOURNAL OF ORGANIC CHEMISTRY,88(20),14670-14675.
MLA Zhu, Jin-xin,et al."Enantioselective Synthesis of 2,3,3a,8a-Tetrahydrofuro[2,3-b]benzofuran Scaffolds Enabled by Cu(II)/SPDO-Catalyzed [3+2] Cycloaddition of 2,3-Dihydrofuran and Quinone Esters".JOURNAL OF ORGANIC CHEMISTRY 88.20(2023):14670-14675.
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