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

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

doi:10.1002/cjoc.202400328

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (18) : 2197 -2202. DOI: 10.1002/cjoc.202400328

Concise Report

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

Jie Wang ¹
, Hang Qin ¹
, Ya-Li Song ¹^,²
, Fei Cao ¹^,²
, Zhi-Hao You ¹^,²^,^†

Author information +

History +

PDF

Abstract

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 retro-reaction mechanism was discovered in the synthetic transformations of products.

Keywords

Asymmetric catalysis / Organocatalysis / Cyclization / Quintuple reaction / Polycycles / Heterocycles / Chromane / One-pot reaction

Cite this article

Download citation ▾

Jie Wang, Hang Qin, Ya-Li Song, Fei Cao, Zhi-Hao You. Enantioselective Construction of Polycyclic Chromanes through Organocatalytic Sequential Quintuple Reaction via One-Pot Step-Wise Procedure. Chinese Journal of Chemistry, 2024, 42(18): 2197-2202 DOI:10.1002/cjoc.202400328