Journal
ORGANIC LETTERS
Volume 24, Issue 48, Pages 8837-8842Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03601
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Funding
- National Natural Science Foundation of China [22071242, 22173083, 21871260]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- Fujian Natural Science Foundation [2021J01522]
- Open Fund of Guangdong Provincial Key Laboratory of Functional Supra-molecular Coordination Materials and Applications [2020B08]
- Fundamental Research Funds [11620416, 202201020559]
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In this work, the I-2-catalyzed oxa-Nazarov cyclization-Michael addition cascade between vinyl alpha-diketones and enones has been developed, providing a range of functionalized dihydrofuranones with good to high yields. Further transformations on the products have also been achieved. Mechanistic studies reveal the simultaneous occurrence of 1,2-hydride shift during dihydrofuranone formation.
The Nazarov cyclization has been established as a powerful tool in constructing cyclopentenone skeletons. In sharp contrast, oxa-Nazarov cyclization that affords dihydrofuranones, a new type of product, has been less explored. In this work, we report the I-2-catalyzed oxa-Nazarov cyclization-Michael addition cascade between vinyl alpha-diketones and enones. The protocol allows access to a range of functionalized dihydrofuranones with good to high yields, and diverse further transformations on the products have been achieved. Furthermore, the mechanistic studies reveal that the 1,2-hydride shift occurs simultaneously during the dihydrofuranone formation.
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