4.6 Article

Sc(OTf)3-mediated 1,3-dipolar cycloaddition-ring cleavage-rearrangement: a highly stereoselective access to Z-β-enaminonitriles

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 2, Pages 513-519

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob01801j

Keywords

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Funding

  1. Ministry of Education of China [IRT1225]
  2. National Natural Science Foundation of China [21362002, 41206077, 81260472]
  3. State Key Laboratory Cultivation Base for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China [CMEMR2014-A02, CMEMR2012-A, CMEMR2013-C01]
  4. Bagui Scholar Program of Guangxi

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A novel and highly stereoselective synthesis of Z-beta-enaminonitriles from azides and alpha,beta-unsaturated nitriles is reported. The reaction proceeds via a 1,3-dipolar cycloaddition-ring cleavage-rearrangement cascade mediated by a catalytic amount of Sc(OTf)(3). A plausible reaction mechanism for this process is depicted.

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