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Synfacts 2011(4): 0411-0411  
DOI: 10.1055/s-0030-1259655
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Addition of Pyrazolones to Dialkyl Azodicarboxylates

Contributor(s): Mark Lautens, Jane Panteleev
Z. Yang, Z. Wang, S. Bai, X. Liu, L. Lin, X. Feng*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
18 March 2011 (online)

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Significance

Rare-earth metal triflates are now commonly applied in Lewis acid catalyzed reactions and are often utilized in asymmetric catalysis (see Review below). The authors employ a gadolinium-N,N′-dioxide complex in the α-amination of pyrazolones with azadiacarboxylates. α-Amination of similar nucleophiles and electrophiles is known; however, the authors add to the field by utilizing a catalyst capable of higher turnover numbers, and therefore, potential for scale-up. This method accesses tertiary amines in high yields and enantio­selectivities.

Review: S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.-L. Lam. Chem. Rev. 2002, 102, 2227-2302.