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Synthesis 2011(18): 2959-2967  
DOI: 10.1055/s-0030-1260150
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Metal-Free Intramolecular Aziridination of Allylic Carbamates Mediated by Hypervalent Iodine Compounds

Qing-Hai Denga, Jing-Cui Wanga, Zhen-Jiang Xu*a, Cong-Ying Zhoub, Chi-Ming Che*a,b
a Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 345 Ling Ling Road, Shanghai, P. R. of China
e-Mail: xuzhenjiang@mail.sioc.ac.cn;
b Department of Chemistry, State Key Laboratory of Synthetic Chemistry, and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China
Fax: +85228571586; e-Mail: cmche@hku.hk;
Further Information

Publication History

Received 17 May 2011
Publication Date:
05 August 2011 (online)

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Abstract

An efficient and practical hypervalent iodine compound mediated metal-free intramolecular aziridination reaction of allylic carbamates was developed. Analytically pure aziridines were obtained in high yields by simple filtration of the reaction mixture. In situ ring opening of the aziridines provides an easy access to useful vicinal amino alcohol derivatives and diamine compounds. Up to 16% ee was obtained when chiral hypervalent iodine compound was used.

Key words

aziridination - hypervalent iodine - allylic carbamate - ring opening - vicinal diamine

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