Issue 8, 2022

Diastereoselective synthesis of 1,1,3,3-tetrasubstituted cyclobutanes enabled by cycloaddition of bicyclo[1.1.0]butanes

Abstract

Bicyclo[1.1.0]butanes (BCBs), a class of highly strained saturated bicyclic carbocycles, have garnered increasing attention in recent years. Functionalization of BCBs provides an efficient approach to access cyclobutane derivatives driven by a strain-releasing force. We report here a diastereoselective synthesis of multi-substituted cyclobutanes through the cycloaddition of BCBs with triazolinedione or nitrosoarenes. The subsequent cleavage of NN or NO bonds of cycloadducts provides cyclobutane derivatives containing cis-1,3-heteroatom substitutions.

Graphical abstract: Diastereoselective synthesis of 1,1,3,3-tetrasubstituted cyclobutanes enabled by cycloaddition of bicyclo[1.1.0]butanes

Supplementary files

Article information

Article type
Research Article
Submitted
31 jan 2022
Accepted
01 mar 2022
First published
10 mar 2022

Org. Chem. Front., 2022,9, 2149-2153

Diastereoselective synthesis of 1,1,3,3-tetrasubstituted cyclobutanes enabled by cycloaddition of bicyclo[1.1.0]butanes

M. Wang, Y. Huang, C. Li and P. Lu, Org. Chem. Front., 2022, 9, 2149 DOI: 10.1039/D2QO00167E

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