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

Peiming Gu; Xiu-Ping Wu; Yan Su; Xue-Qiang Li; Ping Xue; Rui Li

doi:10.1055/s-0033-1340173

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(4): 535-538
DOI: 10.1055/s-0033-1340173

letter

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

Peiming Gu*

^aKey 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

^aKey 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

^bState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China

,

Xue-Qiang Li

^aKey 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

^aKey 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

^aKey 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

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Abstract

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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.

Key words

azides - carbenoids - diazo compounds - imines - esters - catalysis - rhodium

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Referenzen

References
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