Synthesis 2020; 52(20): 2979-2986
DOI: 10.1055/s-0040-1707205
paper
© Georg Thieme Verlag Stuttgart · New York

Application of Benzofuran-Derived Azadienes as Two-Carbon Building Blocks in Annulations: Chemo- and Diastereoselective Construction of Spiro-Benzofuran Scaffolds

Ye-Xin Wang
a   School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China   eMail: fshi@jsnu.edu.cn   eMail: wtan@jsnu.edu.cn
,
Yi-Nan Lu
a   School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China   eMail: fshi@jsnu.edu.cn   eMail: wtan@jsnu.edu.cn
,
Lin-Lin Xu
b   Key Lab of Environment and Health, School of Public Health, Xuzhou Medical University, Xuzhou 221006, P. R. of China   eMail: xiaopangpeng@126.com
,
Feng-Tao Sheng
a   School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China   eMail: fshi@jsnu.edu.cn   eMail: wtan@jsnu.edu.cn
,
Jin-Peng Zhang
b   Key Lab of Environment and Health, School of Public Health, Xuzhou Medical University, Xuzhou 221006, P. R. of China   eMail: xiaopangpeng@126.com
,
Wei Tan
a   School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China   eMail: fshi@jsnu.edu.cn   eMail: wtan@jsnu.edu.cn
,
Feng Shi
a   School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, P. R. of China   eMail: fshi@jsnu.edu.cn   eMail: wtan@jsnu.edu.cn
› Institutsangaben
We very much appreciate the financial support from National Natural Science Foundation of China (21772069 and 21831007), Six Kinds of Talents Project of Jiangsu Province (SWYY-025), TAPP, and Undergraduate Students Project of JSNU.
Weitere Informationen

Publikationsverlauf

Received: 08. Juni 2020

Accepted after revision: 25. Juni 2020

Publikationsdatum:
15. Juli 2020 (online)


§ These authors contributed equally to this work.

Abstract

A base-promoted (2+4) annulation of benzofuran-derived azadienes with para-quinone methide derivatives has been established, which afforded spiro-benzofuran derivatives in generally high yields (57–97%) and with good diastereoselectivities (85:15 to >95:5 dr). This reaction not only represents the first application of benzofuran-derived azadienes as two-carbon building blocks in annulations, but also provides an efficient protocol for the construction of spiro-benzofuran scaffolds with chemoselectivity and high diastereoselectivity. This approach will enrich the chemistry of benzofuran-derived azadiene-involved reactions.

Supporting Information

 
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        1919
      • 19a CCDC 2007585 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
      • 19b See the Supporting Information for details.