Synthesis of Planar Chiral [2.2]Paracyclophanyl Imidazo[1,5-a]pyridinium Salts for the Rhodium-Catalyzed Asymmetric Arylation

Several novel flexibility-restricted imidazo[1,5-a]pyridinium triflates (abbreviated as imidazolium salts) were synthesized from (4S p ,13R p )-(−)-4-amino-13-bromo[2.2]paracyclophane and pyridylaldehyde. These imidazolium salts can be used as nitrogen-containing heterocyclic carbene precursors in a...

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Bibliographic Details
Published in:Synthetic communications 2013-02, Vol.43 (6), p.810-825
Main Authors: Wang, Dengxia, Ma, Yudao, He, Fuyan, Duan, Wenzeng, Zhao, Lei, Song, Chun
Format: Article
Language:English
Subjects:
[2.2]paracyclophane
Aldehyde
asymmetric arylation
N-heterocyclic carbene
planar chirality
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Summary:Several novel flexibility-restricted imidazo[1,5-a]pyridinium triflates (abbreviated as imidazolium salts) were synthesized from (4S p ,13R p )-(−)-4-amino-13-bromo[2.2]paracyclophane and pyridylaldehyde. These imidazolium salts can be used as nitrogen-containing heterocyclic carbene precursors in asymmetric catalysis and here they are applied in the Rh-catalyzed asymmetric 1,2-addition of arylboronic acids to aldehydes. After optimizing the catalytic situations and testing a series of substrates, moderate enantioselectivity and good yield were obtained.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2011.610548