Oxime Radical Promoted Dioxygenation, Oxyamination, and Diamination of Alkenes: Synthesis of Isoxazolines and Cyclic Nitrones†
Corresponding Author
Prof. Dr. Bing Han
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)Search for more papers by this authorXiu-Long Yang
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorDr. Ran Fang
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorProf. Dr. Wei Yu
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorChao Wang
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorXiao-Yong Duan
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorShuai Liu
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Bing Han
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)Search for more papers by this authorXiu-Long Yang
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorDr. Ran Fang
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorProf. Dr. Wei Yu
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorChao Wang
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorXiao-Yong Duan
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorShuai Liu
State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University, Lanzhou 730000 (P.R. China)
Search for more papers by this authorWe are grateful for financial support from the NSFC (Nos. 20902040 and J1103307), the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT1138), the 111 Project, and the Fundamental Research Funds for the Central Universities (lzujbky-2012-61).
Graphical Abstract
Up the tempo: The intramolecular addition of oxime radicals to CC bonds was achieved by using DEAD and TEMPO to give 4,5-dihydroisoxazoles as a result of a CO bond-forming, 5-exo-trig cyclization. γ,δ-Unsaturated ketoximes also reacted to afford cyclic nitrones through CN bond formation. The reactions offer a metal-free approach for the vicinal difunctionalization of unactivated alkenes.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
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