Enantioselective synthesis of triarylmethanes by chiral imidodiphosphoric acids catalyzed Friedel-Crafts reactions.
The first enantioselective synthesis of pyrrolyl-substituted triarylmethanes has been accomplished using a novel imidodiphosphoric acid catalyst, which is derived from two (R)-BINOL frameworks with different 3,3'-substituents. This strategy was also expanded to the synthesis of bis(indolyl)-substituted triarylmethanes with high enantioselectivities, which could only be obtained with moderate ee values in previous reports. These two efficient Friedel-Crafts alkylation processes feature low catalyst loading, broad functional group compatibilities, and the potential to provide practical pathways for the synthesis of enantioenriched bioactive triarylmethanes.
College of Chemistry, Jilin University , 2699 Qianjin Street, Changchun 130012, China.
Ming-Hua
MH
Zhuo
Yi-Jun
YJ
Jiang
Yan-Sen
YS
Fan
Yang
Y
Gao
Song
S
Liu
Suoqin
S
Zhang
D000478:Alkylation; D002384:Catalysis; D004164:Diphosphonates / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D004164:Diphosphonates; D007211:Indoles; C016514:imidodiphosphonic acid; D008697:Methane