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Synlett 2005(9): 1429-1432  
DOI: 10.1055/s-2005-868498
LETTER
© Georg Thieme Verlag Stuttgart · New York

The First Example of Catalytic Aziridination Mediated by Arsonium Ylides: Preparation of trans-Pentafluorophenyl-Containing Aziridines

Shifa Zhua, Yuanxi Liaoa, Shizheng Zhu*a,b
a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 20032, P. R. China
b College of Chemical Environmental, South China Normal University, Guangzhou, 510631, P. R. China
Fax: +86(21)64166128; e-Mail: zhusz@mail.sioc.ac.cn;
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Publication History

Received 25 February 2005
Publication Date:
27 April 2005 (online)

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Abstract

Triphenylarsine catalyzes the formation of aziridines from tosyl imines and aromatic diazo compounds in a one-pot reaction. It is the first example of catalytic aziridination mediated by ­arsonium ylides. It gave aziridines in excellent diastereoselectivity with pentafluorophenyl diazomethane as the substrate. This catalytic reaction is complementary with the reaction mediated by sulfur ylides.

Key words

diazocompound - ylide - fluorine - aziridine - catalyze

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