4.8 Article

Development of Tartaric Acid Derived Chiral Guanidines and Their Application to Catalytic Enantioselective α-Hydroxylation of β-Dicarbonyl Compounds

Journal

ORGANIC LETTERS
Volume 15, Issue 12, Pages 3106-3109

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol401306h

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Funding

  1. National Natural Science Foundation of China [21076035, 20972022]
  2. Program for New Century Excellent Talents in University [NCET-11-0053]
  3. Fundamental Research Funds for the Central Universities [DUT13ZD202]
  4. Science and Technology Department of Liaoning Province [20102032]

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A novel library of chiral guanidines featuring a tartaric acid skeleton was developed from diethyl L-tartrate. These guanidines are easily accessed with tunable style and electronic properties. The utilities of the guanidines were highlighted by their ability to catalyze the alpha-hydroxylation of beta-ketoesters and beta-diketones with remarkable efficiency and excellent enantioselectivity.

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