Synlett 2012; 23(12): 1801-1804
DOI: 10.1055/s-0031-1289786
letter
© Georg Thieme Verlag Stuttgart · New York

The Oxidative Acylnitroso Hetero-Diels–Alder Reaction Catalyzed by Dirhodium Caprolactamate

Xiarepati Tusun
a  Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, P. R. of China
b  Graduate University of the Chinese Academy of Sciences, Beijing 100049, P. R. of China, Fax: +86(991)3838708   Email: clu@ms.xjb.ac.cn
,
Chong-Dao Lu*
a  Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 07 April 2012

Accepted after revision: 09 May 2012

Publication Date:
29 June 2012 (online)


Abstract

An effective protocol is described for the generation and in situ Diels–Alder trapping of acylnitroso derivatives. In this procedure, the oxidation of hydroxamic acid is efficiently catalyzed by dirhodium(II) caprolactamate with tert-butyl hydroperoxide (TBHP) in the presence of dienes at room temperature. Using this approach we obtained a variety of hetero-Diels–Alder cycloadducts in yields of up to 96% at 0.1 mol% catalyst loading.

Supporting Information

 
  • References

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