Chinese Journal of Organic Chemistry >
Studies on the Asymmetric Catalytic Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by Heteroarylidene-BOX-Cu Complexes
Received date: 2015-05-07
Revised date: 2015-06-08
Online published: 2015-06-16
Supported by
Project supported by the National Natural Science Foundation of China (Nos. J1210064, 21172255).
This paper reported the reaction of indoles with trifluoromethyl pyruvate catalyzed by heteroaryliden-tethered bis-oxazoline-Cu(II) complex, and the effects of ligand structure, solvent, temperature and different indole substrates on the catalytic reactions were investigated. The results indicate that the reaction furnished high reactivity and moderate to good enantioselectivity, and the substituents on the indole ring have important impact on the reaction. The reaction can afford the indole derivatives with a chiral tertiary carbon center bearing trifluoromethyl substituent in high yields with moderate to good enantioselectivities.
Key words： trifluoromethyl; Friedel-Crafts; indole; bis-oxazoline
Yin Bohan , Wu Yanhua , Ma hongli , Ma Xiaodong , Fu Bin , Liu Jiping . Studies on the Asymmetric Catalytic Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by Heteroarylidene-BOX-Cu Complexes[J]. Chinese Journal of Organic Chemistry, 2015 , 35(10) : 2119 -2124 . DOI: 10.6023/cjoc201505013
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