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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:youzhihao@hbu.edu.cn

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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.
Submitted to Chinese Journal of Chemistry
28 Mar 2024Submission Checks Completed
28 Mar 2024Assigned to Editor
28 Mar 2024Review(s) Completed, Editorial Evaluation Pending
09 Apr 2024Editorial Decision: Revise Minor
25 Apr 20241st Revision Received
25 Apr 2024Submission Checks Completed
25 Apr 2024Assigned to Editor
25 Apr 2024Review(s) Completed, Editorial Evaluation Pending
25 Apr 2024Editorial Decision: Accept