Asymmetric Organocatalytic Synthesis of Chiral Polycyclic 1,4‐Dihydropyridines and Axially Chiral 4‐Arylpyridines Using 2,3‐Dioxopyrrolidines and 1,3‐Diketones | Zendy

Ou ChengYu | Zendy; Huang BoWei | Zendy; Chu TingHung | Zendy; Lin PoHeng | Zendy; Han JengLiang | Zendy

Premium

Asymmetric Organocatalytic Synthesis of Chiral Polycyclic 1,4‐Dihydropyridines and Axially Chiral 4‐Arylpyridines Using 2,3‐Dioxopyrrolidines and 1,3‐Diketones

Author(s) -

Ou ChengYu,

Huang BoWei,

Chu TingHung,

Lin PoHeng,

Han JengLiang

Publication year - 2025

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.202500205

Subject(s) - chemistry , organocatalysis , enantioselective synthesis , combinatorial chemistry , organic chemistry , chirality (physics) , axial symmetry , computational chemistry , stereochemistry , catalysis , chiral symmetry , physics , quantum mechanics , quark , nambu–jona lasinio model

Abstract An asymmetric Michael/hemiketalization/amination reaction of 1,3‐diketones with 2,3‐dioxopyrrolidines catalysed by a quinine‐derived urea catalyst has been developed, which furnished a series of chiral polycyclic 1,4‐dihydropyridines in satisfactory yields and enantioselectivities (35–94 % yield for two steps and up to 99 % ee). Moreover, the subsequent oxidative aromatization of chiral 1,4‐dihydropyridines delivered chiral atropisomeric 4‐arylpyridines in 69–94 % yield and up to 95 % ee.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research