Synthesis 2013; 45(21): 2959-2965
DOI: 10.1055/s-0033-1339378
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

An Efficient Method for Opening N-Tosylaziridines with Silylated Nucleo­philes by Using Polystyrene-Supported 1,5,7-Triazabicyclo[4.4.0]dec-5-ene as a Reusable Organocatalyst

Satoru Matsukawa*
Department of Science Education, Faculty of Education, Ibaraki University, 2-1-1 Bunkyo, Mito, Ibaraki, 310-8512, Japan   Fax: +81(29)228 8234   Email: [email protected]
,
Kumiko Tsukamoto
Department of Science Education, Faculty of Education, Ibaraki University, 2-1-1 Bunkyo, Mito, Ibaraki, 310-8512, Japan   Fax: +81(29)228 8234   Email: [email protected]
,
Shiori Yasuda
Department of Science Education, Faculty of Education, Ibaraki University, 2-1-1 Bunkyo, Mito, Ibaraki, 310-8512, Japan   Fax: +81(29)228 8234   Email: [email protected]
,
Takeru Harada
Department of Science Education, Faculty of Education, Ibaraki University, 2-1-1 Bunkyo, Mito, Ibaraki, 310-8512, Japan   Fax: +81(29)228 8234   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 14 June 2013

Accepted: 21 June 2013

Publication Date:
12 August 2013 (online)


Abstract

Polystyrene-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (PS-TBD) catalyzes the ring opening of N-tosylaziridines with trimethylsilyl cyanide, trimethylsilyl azide, or trimethylsilyl halides to give the corresponding products in high yields. PS-TBD can be easily recovered and reused without significant loss of catalytic activity.

Supporting Information

 
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