Rh(II)-Catalyzed Ring Expansion of Cyclopropyl N-Tosylhydrazones to 1-Substituted Cyclobutenes
Wenbai Ouyang, Jingfeng Huo*, Jianbo Wang*
*Key Laboratory of Bioorganic Chemistry and Molecular
Engineering, Peking University, Beijing 100871, P. R. of China, Email:
jingfenghuouchicago.edu, wangjb
pku.edu.cn
W. Ouyang, J. Huo, J. Wang, Synlett, 2023, 34, 1507-1511.
DOI: 10.1055/a-1995-5960
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Abstract
Cyclobutenes are highly useful synthetic intermediates as well as important motifs in functional molecules. A Rh-catalyzed ring expansion of cyclopropyl N-tosylhydrazone enables a straightforward synthesis of monosubstituted cyclobutenes. 1,2-Aryl or -alkyl shift of the Rh(II) carbene intermediate plays the key role in this transformation.
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Key Words
Rh(II) catalysis, N-tosylhydrazones, 1,2-shift, metal carbenes, cyclobutenes, cyclopropanes
ID: J72-Y2023