Regioselective Bromocyclization of Unsaturated N-Tosylcarbamates Promoted by N,N-Dibromosulfonamides

Guo-Tao Fan; Ming-Hui Sun; Ge Gao; Jie Chen; Ling Zhou

doi:10.1055/s-0034-1378314

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(13): 1921-1925
DOI: 10.1055/s-0034-1378314

letter

Regioselective Bromocyclization of Unsaturated N-Tosylcarbamates Promoted by N,N-Dibromosulfonamides

Authors

Guo-Tao Fan

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, P. R. of China Fax: +86(29)88303915 eMail: chmchenj@nwu.edu.cn eMail: zhoul@nwu.edu.cn
Ming-Hui Sun

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, P. R. of China Fax: +86(29)88303915 eMail: chmchenj@nwu.edu.cn eMail: zhoul@nwu.edu.cn
Ge Gao

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, P. R. of China Fax: +86(29)88303915 eMail: chmchenj@nwu.edu.cn eMail: zhoul@nwu.edu.cn
Jie Chen*

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, P. R. of China Fax: +86(29)88303915 eMail: chmchenj@nwu.edu.cn eMail: zhoul@nwu.edu.cn
Ling Zhou*

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an 710069, P. R. of China Fax: +86(29)88303915 eMail: chmchenj@nwu.edu.cn eMail: zhoul@nwu.edu.cn

Abstract

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Abstract

Simple and highly regioselective bromo-N-cyclization and bromo-O-cyclization reactions of unsaturated N-tosylcarbamates have been developed. The use of N,N-dibromosulfonamides as brominating reagents plays an important role in these electrophilic cyclization reactions. This method is useful in organic synthesis. The desired products can be smoothly transformed into aziridines or epoxides.

Key words

alkenes - amides - cyclizations - electrophilic additions - regioselectivity

Volltext

Referenzen

References

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11 The details appear in the Supporting Information.
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Zusatzmaterial

Supporting Information (PDF)