Organic Chemistry Portal

Abstracts

Search:

Lewis Acid-Catalyzed Selective [2 + 2]-Cycloaddition and Dearomatizing Cascade Reaction of Aryl Alkynes with Acrylates

Liang Shen, Kai Zhao, Kazuki Doitomi, Rakesh Ganguly, Yong-Xin Li, Zhi-Liang Shen*, Hajime Hirao and Teck-Peng Loh*

*Nanjing Tech University, Nanjing, Jiangsu, P. R. China, 210009; Nanyang Technological University, Singapore, 637371, Email: ias_zlshennjtech.edu.cn, teckpengntu.edu.sg

L. Shen, K. Zhao, K. Doitomi, R. Ganguly, Y.-X. Li, Z.-L. Shen, H. Hirao, T.-P. Loh, J. Am. Chem. Soc., 2017, 139, 13570-13578.

DOI: 10.1021/jacs.7b07997 (free Supporting Information)


see article for more reactions

Abstract

An In(tfacac)3-TMSBr catalyzed selective [2 + 2]-cycloaddition enables an efficient synthesis of cyclobutenes from aryl alkynes and acrylates with high chemo- and stereoselectivity. Densely functionalized decalin skeletons can be produced through a dearomatizing cascade reaction. The obtained cyclobutenes could be easily converted into cyclobutanes as well as synthetically useful 1,4- and 1,5-diketones with high chemo- and stereoselectivity.

see article for more examples

proposed mechanism



Key Words

cyclobutenes


ID: J48-Y2017