Synthetic and Computational Study of the Enantioselective [3+2]-Cycloaddition of Chromones with MBH Carbonates,Organic Letters

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Synthetic and Computational Study of the Enantioselective [3+2]-Cycloaddition of Chromones with MBH Carbonates
Organic Letters ( IF 4.9 ) Pub Date : 2022-08-04 , DOI: 10.1021/acs.orglett.2c01922
Ling Meng _{1,

2,

3,

4} , Heyang Liu ₃ , Zhenyang Lin ₂ , Jun Wang _{1,

4}

Affiliation

Highly efficient and straightforward access to enantioenriched five-membered ring-fused chromanones is developed via [3+2]-cycloaddition of 3-cyanochromones with Morita–Baylis–Hillman carbonates. Densely functionalized chiral cyclopenta[b]chromanones with three continuous quaternary and tertiary stereogenic carbon centers were obtained in high yields with high ee and dr (≤97% yield, 97% ee, and >20:1 dr). Moreover, density functional theory calculations have been carried out to investigate the mechanism and regio- and diastereoselectivity of the reaction.

中文翻译：

色分子与 MBH 碳酸酯的对映选择性 [3+2]-环加成的合成和计算研究

通过 3-氰基色酮与 Morita-Baylis-Hillman 碳酸盐的 [3+2]-环加成，开发了高效且直接地获得对映体富集的五元环稠合色酮。以高产率和高 ee 和 dr （ ≤97% 产率、97% ee 和 >20:1 dr）获得了具有三个连续四元和叔立体碳中心的密集官能化手性环戊二烯色酮。此外，已经进行了密度泛函理论计算以研究反应的机理以及区域和非对映选择性。

更新日期：2022-08-04

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