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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Sc(OTf)3-mediated 1,3-dipolar cycloaddition-ring cleavage-rearrangement: a highly stereoselective access to
Ying-chun Wang1, Yu-yang Xie, Xian-chun Tan
1Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin 541004, People's Republic of China. whengshan@163.com panym2013@hotmail.com.
Abstract:
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.
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