Enantioselective Construction of Polycyclic Chromanes through Organocatalytic Sequential Quintuple Reaction via One-Pot Step-Wise Procedure

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外文摘要：An efficient and highly stereoselective synthetic method to access polycyclic chromanes has been achieved through organocatalyzed one-pot step-wise reactions involving 2-hydroxycinnamaldehydes,2-aminochalcones,and malononitrile as substrates.The reactions underwent a quintuple process by aza-Michael/Michael/Knoevenagel/oxa-Michael/aldol-type reaction in sequence to give products bearing 3 new generated rings and 5 chiral centers in moderate to quantitative yields with excellent stereoselectivities.A novel ret-ro-reaction mechanism was discovered in the synthetic transformations of products.

外文关键词：

Asymmetric catalysisOrganocatalysisCyclizationQuintuple reactionPolycyclesHeterocyclesChromaneOne-pot reaction

作者：

Jie Wang、Hang Qin、Ya-Li Song、Fei Cao、Zhi-Hao You

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作者单位：

Key Laboratory of Pharmaceutical Quality Control of Hebei Province,College of Pharmaceutical Sciences,Hebei University,Baoding,Hebei 071002,China

Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education,Baoding,Hebei 071002,China

出版年：

2024

DOI：

10.1002/cjoc.202400328