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Synfacts 2010(8): 0907-0907  
DOI: 10.1055/s-0030-1257828
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Zirconium-Mediated Enantioselective Darzens Reaction

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
L. He, W.-J. Liu, L. Ren, T. Lei, L.-Z. Gong*
University of Science and Technology of China, Hefei, P. R. of China
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

Enantiomerically enriched glycidic esters and amides constitute an important class of building blocks for organic synthesis. The Darzens reaction represents a powerful approach towards these compounds; however, limited success has been achieved for asymmetric versions of the process. The authors have developed an air-staible zirconium-based catalytic system, which allowed the formation of glycidic amides with 64-97% yields and 91 to >99% ee. cis-Adducts were formed exclusively. This methodology is advantageous to titanium-based systems with regard to lesser sensitivity to air and moisture. A wide range of substrates was tolerated including aromatic, heteroaromatic, and aliphatic aldehydes.