Catalytic asymmetric Friedländer condensation to construct cyclobutanone-fused quinolines with a quaternary stereogenic centre

The first catalytic desymmetric Friedländer condensation of 2-aminobenzophenone with prochiral cyclobutane-1,3-dione has been achieved using chiral phosphoric acid catalysis. A series of cyclobutanone-fused quinolines with quaternary stereogenic centres were obtained in up to 98% yield and 94% ee.

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2024-09, Vol.11 (19), p.5363-5367
Main Authors: Li-E, Wang, Zhang, Si, Ruo-Shi, Jin, Yi-Yuan, Peng, Qiu-Ping, Ding, Xing-Ping Zeng
Format: Article
Language:English
Subjects:
Catalysis
Cyclobutane
Diketones
Organic compounds
Phosphoric acid
Quinolines
Online Access:Get full text
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Description
Summary:The first catalytic desymmetric Friedländer condensation of 2-aminobenzophenone with prochiral cyclobutane-1,3-dione has been achieved using chiral phosphoric acid catalysis. A series of cyclobutanone-fused quinolines with quaternary stereogenic centres were obtained in up to 98% yield and 94% ee.
ISSN:2052-4110
2052-4110
DOI:10.1039/d4qo01177e