Synlett 2014; 25(4): 535-538
DOI: 10.1055/s-0033-1340173
letter
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Intermolecular Reaction of Alkyl Azides with Diazo(aryl)acetates

Peiming Gu*
a   Key Laboratory of Energy Sources & Engineering, State Key Laboratory Cultivation Base of Natural Gas Conversion and Department of Chemistry, Ningxia University, Yinchuan 750021, P. R. of China   Fax: +86(951)2062323   Email: gupm@nxu.edu.cn
,
Xiu-Ping Wu
a   Key Laboratory of Energy Sources & Engineering, State Key Laboratory Cultivation Base of Natural Gas Conversion and Department of Chemistry, Ningxia University, Yinchuan 750021, P. R. of China   Fax: +86(951)2062323   Email: gupm@nxu.edu.cn
,
Yan Su
b   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
,
Xue-Qiang Li
a   Key Laboratory of Energy Sources & Engineering, State Key Laboratory Cultivation Base of Natural Gas Conversion and Department of Chemistry, Ningxia University, Yinchuan 750021, P. R. of China   Fax: +86(951)2062323   Email: gupm@nxu.edu.cn
,
Ping Xue
a   Key Laboratory of Energy Sources & Engineering, State Key Laboratory Cultivation Base of Natural Gas Conversion and Department of Chemistry, Ningxia University, Yinchuan 750021, P. R. of China   Fax: +86(951)2062323   Email: gupm@nxu.edu.cn
,
Rui Li
a   Key Laboratory of Energy Sources & Engineering, State Key Laboratory Cultivation Base of Natural Gas Conversion and Department of Chemistry, Ningxia University, Yinchuan 750021, P. R. of China   Fax: +86(951)2062323   Email: gupm@nxu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 19 September 2013

Accepted after revision: 10 December 2013

Publication Date:
14 January 2014 (online)


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Abstract

An efficient intermolecular interception of alkyl azides by diazo(aryl)acetates was achieved in the presence of dirhodium tetraoctanoate. The initial products were unstable α-imino esters, and overaddition of carbenoids to the C–N double bonds was avoided. After acidic workup, the corresponding α-keto esters were obtained in good to excellent yields.

Supporting Information