Catalytic asymmetric aza Diels-Alder reactions of hydrazones using a chiral zirconium catalyst |
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Authors: | Yasuhiro Yamashita |
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Institution: | Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan |
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Abstract: | Catalytic asymmetric aza Diels-Alder reactions of acylhydrazones with Danishefsky’s dienes have been developed. A chiral zirconium complex derived from zirconium propoxide and 3,3′,6,6′-I4BINOL was found to be effective in this reaction, and the desired optically active 2,3-dihydro-4-pyridone derivatives were obtained with high enantioselectivities. Asymmetric formal synthesis of a natural product, coniine, was conducted using this catalytic asymmetric reaction as a key step. |
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Keywords: | Zirconium Lewis acid Asymmetric Hydrazone Aza Diels-Alder reaction |
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