Synlett 2015; 26(13): 1827-1830
DOI: 10.1055/s-0034-1381008
letter
© Georg Thieme Verlag Stuttgart · New York

Convenient Synthesis of N-Tosyl-2-(difluoromethyl)aziridine and Its Application to the Preparation of Difluoromethyl-β-tryptamine Analogues

Fumihiro Kurosato
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjyo-machi 1, Saga 840-8502, Japan   Email: hanamoto@cc.saga-u.ac.jp
,
Takuya Ishikawa
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjyo-machi 1, Saga 840-8502, Japan   Email: hanamoto@cc.saga-u.ac.jp
,
Yasunori Yamada
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjyo-machi 1, Saga 840-8502, Japan   Email: hanamoto@cc.saga-u.ac.jp
,
Takeshi Hanamoto*
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjyo-machi 1, Saga 840-8502, Japan   Email: hanamoto@cc.saga-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 23 April 2015

Accepted after revision: 26 May 2015

Publication Date:
14 July 2015 (online)


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Abstract

N-Tosyl-2-(difluoromethyl)aziridine was easily prepared from p-toluenesulfonamide (TsNH2) and β-(difluoromethyl) vinyl sulfonium salt in excellent yield. The reaction of the aziridine and a wide range of indoles in the presence of Et2Zn proceeded smoothly to give the corresponding difluoromethyl-β-tryptamine analogues in good to excellent yields and with excellent regioselectivity.

Supporting Information