4.7 Article

Enantioselective Organocatalytic Biginelli Reaction: Dependence of the Catalyst on Sterics, Hydrogen Bonding, and Reinforced Chirality

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JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 2, 页码 396-402

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AMER CHEMICAL SOC
DOI: 10.1021/jo101717m

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  1. DST, India
  2. CSIR, India

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From a systematic investigation involving the synthesis of a series of catalysts and screening studies, the organocatalyst 16, which is sterically hindered, contains a strong hydrogen-bonding site, and is endowed with reinforced chirality, is shown to promote the Biginelli cyclocondensation of aromatic as well as aliphatic aldehydes with ethyl acetoacetate and urea in a remarkably high enantioselectivity (ee ca. 94-99%).

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