Oxa-Nazarov Cyclization-Michael Addition Sequence for the Rapid Construction of Dihydrofuranones

作者：Chen, Ting; Gong, Fan; Nagaraju, Sakkani^*; Liu, Jinggong^*; Yang, Shuang; Chen, Xingkuan^*; Fang, Xinqiang^*

来源：Organic Letters, 2022, 24(48): 8837-8842.

DOI：10.1021/acs.orglett.2c03601

• ELECTROCYCLIZATION
• CYCLOPENTENONES
• DIKETONES

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.

• 单位
  福州大学; 广州中医药大学; xk; 中国科学院福建物质结构研究所; 广东省人民医院; 中国科学院研究生院