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Enantioselective Construction of Polycyclic Chromanes through Organocatalytic Multicomponent Quintuple Reaction via One-pot Sequential Procedure
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  • Jie Wang,
  • Hang Qin,
  • Ya-Li Song,
  • Fei Cao,
  • Zhi-Hao You
Jie Wang
Hebei University
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Hang Qin
Hebei University
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Ya-Li Song
Hebei University
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Fei Cao
Hebei University
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Zhi-Hao You
Hebei University

Corresponding Author:[email protected]

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Abstract

An efficient and highly stereoselective synthetic method access to polycyclic chromanes has been achieved through organocatalyzed three-component 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 enantioselectivities. A novel retro-reaction mechanism was discovered in the synthetic transformations of products.