Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 2, Pages 513-519Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob01801j
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Funding
- Ministry of Education of China [IRT1225]
- National Natural Science Foundation of China [21362002, 41206077, 81260472]
- 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]
- 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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