Chinese Journal of Organic Chemistry >
1,4-Functionalization of 3-En-1-ynes with Alcohols via Zinc-Catalyzed Regioselective N-Oxide Oxidation
Received date: 2019-03-25
Revised date: 2019-04-24
Online published: 2019-05-06
Supported by
Project supported by the Zhejiang Provincal Public Welfare Technology Research Program (No. LGG19B040001), the Taizhou Science and Technology Project (No. 1801gy21), the National Natural Science Foundation of China (Nos. 21572186, 21622204) and the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT).
γ-Hydroxyl or γ-alkoxyl-substituted α,β-unsaturated carbonyls widely exist in a variety of natural products and bioactive molecules. Herein, the realization of 1,4-functionalization of 3-en-1-ynes with alcohols through zinc-catalyzed regioselective N-oxide oxidation is described. This tandem reaction allows the practical synthesis of a range of valuable γ-alkoxyl-substituted-α,β-unsaturated amides in moderate to good yields.
Key words： oxidation; 1,4-functionalization; alkynes; tandem reaction
Zheng Renhua , Guo Haichang , Yang Mingyang , Liu Mengqi , Ye Longwu . 1,4-Functionalization of 3-En-1-ynes with Alcohols via Zinc-Catalyzed Regioselective N-Oxide Oxidation[J]. Chinese Journal of Organic Chemistry, 2019 , 39(6) : 1672 -1680 . DOI: 10.6023/cjoc201903054
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