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

Ting ChenFan GongSakkani NagarajuJinggong LiuShuang YangXingkuan ChenXinqiang Fang
Published in: Organic letters (2022)
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 α-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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