Enantioselective Cascade Reaction for Synthesis of Quinolinones through Synergistic Catalysis Using Cu–Pybox and Chiral Benzotetramisole as Catalysts

In contrast to the well‐studied asymmetric catalyzed synthesis of tetrahydroquinolines, the asymmetric methodologies toward 3,4‐dihydroquinolin‐2‐ones are quite rare. Herein, the first asymmetric cascade reaction is reported between ethynyl benzoxazinanones and mixed‐anhydrides generated from aryl a...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-06, Vol.23 (32), p.7689-7693
Main Authors: Lu, Xuehe, Ge, Luo, Cheng, Cang, Chen, Jie, Cao, Weiguo, Wu, Xiaoyu
Format: Article
Language:English
Subjects:
Acids
Anhydrides
Aromatic compounds
Asymmetry
Bearing
Cascade chemical reactions
Catalysis
Catalysts
Chemical synthesis
Chemistry
Chlorides
copper
cyclization
Enantiomers
Lewis base
Protecting groups
quinolinones
synergistic catalysis
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Summary:In contrast to the well‐studied asymmetric catalyzed synthesis of tetrahydroquinolines, the asymmetric methodologies toward 3,4‐dihydroquinolin‐2‐ones are quite rare. Herein, the first asymmetric cascade reaction is reported between ethynyl benzoxazinanones and mixed‐anhydrides generated from aryl acetic acids and pivaloyl chloride, based on synergistic catalysis. This allowed the formation of attractive 3,4‐dihydroquinolin‐2‐ones bearing two vicinal chiral centers at C3 and C4 in high yields with excellent diastereo‐ and enantioselectivities. A plausible chiral induction model for this reaction was proposed. The utility of this methodology was exemplified by further elaboration of the cyclization products by removal of the N‐protecting groups. Synergistic catalysis: An asymmetric cascade reaction synergistically catalyzed by a Cu–Pybox complex and a benzotetramisole‐type Lewis‐base catalyst is developed, affording 3,4‐dihydroquinolin‐2‐ones bearing two vicinal chiral centers in high yields with excellent stereoselectivities.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201701741