废止
有机化学
有机催化
组合化学
药物化学
级联反应
对映选择合成
角鲨胺
环加成
一锅法合成
作者
Sayan Shee,Soumen Barik,Arghya Ghosh,Akkattu T. Biju
出处
期刊:Organic Letters
[American Chemical Society]
日期:2021-09-29
卷期号:23 (20): 8039-8044
被引量:1
标识
DOI:10.1021/acs.orglett.1c03059
摘要
The [3 + 3] annulation of α,β-unsaturated aldehydes with 2-substituted 1,4-naphthoquinones allowing the facile synthesis of functionalized dihydrocoumarins catalyzed by N-heterocyclic carbene (NHC) is reported. The initially formed NHC-homoenolates underwent an efficient Michael-isomerization-lactonization cascade to furnish the products. Preliminary studies on mechanism shed light on the homoenolate pathway over the intermediacy of the α,β-unsaturated acylazolium intermediates. Moreover, using chiral NHCs, the desired products were formed in up to 49% yield and 99:1 er.
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