Preparation of Cyclic N-tert-Butylsulfonyl Enamines by Rh(II)-Mediated Ring Expansion of α-Diazoesters

Shufeng Chen; Yonghua Zhao; Jianbo Wang

doi:10.1055/s-2006-926449

SPECIALTOPIC

Preparation of Cyclic N-tert-Butylsulfonyl Enamines by Rh(II)-Mediated Ring Expansion of α-Diazoesters

Shufeng Chen, Yonghua Zhao, Jianbo Wang*
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China
e-Mail: wangjb@pku.edu.cn;

Abstract

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Abstract

The anion derived from ethyl diazoacetate adds to N-tert-butylsulfonyl ketimines to give β-tert-butylsulfonylamino α-diazoesters, which are further transformed into cyclic enamines by treatment with Rh₂(OAc)₄, through 1,2-C-C bond migration of a Rh(II) carbene intermediate.

Key words

diazo compounds - Rh(II) carbene - 1,2-C-C bond migration - ring expansion

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References

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