Sc(OTf)3-mediated 1,3-dipolar cycloaddition-ring cleavage-rearrangement: a highly stereoselective access to Z-β-enaminonitrilesElectronic supplementary information (ESI) available: General experimental procedures, and spectral data, NMR spectra, high resolution mass spectra for all compounds, and X-ray crystallographic files (CIF) for 3aa and 3ba. CCDC 1005487 and 1005488. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ob01801j

A novel and highly stereoselective synthesis of Z -β-enaminonitriles from azides and α,β-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 p...

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Main Authors: Wang, Ying-chun, Xie, Yu-yang, Tan, Xian-chun, Wang, Heng-shan, Pan, Ying-ming
Format: Article
Language:English
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Summary:A novel and highly stereoselective synthesis of Z -β-enaminonitriles from azides and α,β-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. In this work, a novel and highly stereoselective synthesis of Z -β-enaminonitriles from azides and α ,β-unsaturated nitriles is reported.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01801j