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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: smatsuka@mx.ibaraki.ac.jp
,
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: smatsuka@mx.ibaraki.ac.jp
,
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: smatsuka@mx.ibaraki.ac.jp
,
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: smatsuka@mx.ibaraki.ac.jp
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Publikationsverlauf

Received: 14. Juni 2013

Accepted: 21. Juni 2013

Publikationsdatum:
12. August 2013 (online)

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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.

Keywords

catalysis - polymers - ring opening - heterocycles - aziridines - sulfonamides

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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