4.7 Article

Asymmetric construction of spirocyclohexanonerhodanines catalyzed by simple diamine derived from chiral tert-leucine

Journal

CHEMICAL COMMUNICATIONS
Volume 48, Issue 73, Pages 9180-9182

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2cc34321e

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Funding

  1. Shanghai Municipal Education Commission [11ZZ56]
  2. National Natural Science Foundation of China [20902018]
  3. Fundamental Research Funds for the Central Universities
  4. Shanghai Committee of Science and Technology [11DZ2260600]

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A diamine-catalyzed asymmetric tandem reaction between alpha,beta-unsaturated ketones and rhodanine derivatives has been developed to synthesize various spirocyclic compounds with high stereoselectivities (up to 99% ee and >20 : 1 dr). The products obtained contain two pharmaceutically relevant features: the biologically active rhodanine moiety embedded in a spirocyclic unit.

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