4.7 Article

Base-Controlled Selective Conversion of Michael Adducts of Malonates with Enones in the Presence of Iodine

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 23, 页码 9809-9816

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AMER CHEMICAL SOC
DOI: 10.1021/jo201879t

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资金

  1. National Natural Science Foundation of China [20902039, 20872051]
  2. Natural Science Foundation of Jiangsu Province [BK2009543]
  3. Jiangsu Higher Education Institutions

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An efficient base-controlled selective conversion of the Michael adducts of malonates with enones in the presence of iodine is reported. Highly functionalized cyclopropane, oxetane, and alpha-hydroxylmalonate derivatives are obtained selectively using DBU, Na2CO3, and NaOAc as the base, respectively. O-2 was identified to be crucial to the formation of oxetane and alpha-hydroxylmalonate derivatives.

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