Chiral Bis(Imidazolidine)Pyridine-Cu Complex-Catalyzed Enantioselective [3+2]-Cycloaddition of Azomethine Imines with Propiolates

doi:10.3390/molecules17056170

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Molecules 2012, 17(5), 6170-6178; doi:10.3390/molecules17056170

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Chiral Bis(Imidazolidine)Pyridine-Cu Complex-Catalyzed Enantioselective [3+2]-Cycloaddition of Azomethine Imines with Propiolates

Takayoshi Arai * and Yuta Ogino

Department of Chemistry, Graduate School of Science, Chiba University, 1-33, Yayoi, Inage, Chiba 263-8522, Japan

* Author to whom correspondence should be addressed.

Received: 27 April 2012; in revised form: 18 May 2012 / Accepted: 21 May 2012 / Published: 24 May 2012

(This article belongs to the Special Issue Asymmetric Catalysis)

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Abstract: [3+2] Cycloaddition of azomethine imines with electron-deficient terminal alkynes was smoothly catalyzed by a chiral bis(imidazolidine)pyridine-CuOAc complex to give bicyclic pyrazolo[1,2-a]pyrazolone derivatives with up to 74% ee.

Keywords: pyrazolone; [3+2] cycloaddition; asymmetric synthesis; catalyst; chiral ligand

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MDPI and ACS Style

Arai, T.; Ogino, Y. Chiral Bis(Imidazolidine)Pyridine-Cu Complex-Catalyzed Enantioselective [3+2]-Cycloaddition of Azomethine Imines with Propiolates. Molecules 2012, 17, 6170-6178.

AMA Style

Arai T, Ogino Y. Chiral Bis(Imidazolidine)Pyridine-Cu Complex-Catalyzed Enantioselective [3+2]-Cycloaddition of Azomethine Imines with Propiolates. Molecules. 2012; 17(5):6170-6178.

Chicago/Turabian Style

Arai, Takayoshi; Ogino, Yuta. 2012. "Chiral Bis(Imidazolidine)Pyridine-Cu Complex-Catalyzed Enantioselective [3+2]-Cycloaddition of Azomethine Imines with Propiolates." Molecules 17, no. 5: 6170-6178.

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