Enantioselective Friedel−Crafts Alkylation of Indoles with Trifluoroethylidene Malonates by Copper−Bis(oxazoline) Complexes: Construction of Trifluoromethyl-Substituted Stereogenic Tertiary Carbon Center

An enantioselective alkylation of indoles with trifluoroethylidene malonates catalyzed by copper(II)−bis (oxazoline) complexes has been developed. The expected adducts with a stereogenic tertiary carbon center bearing a trifluoromethyl group were obtained in excellent yields (up to 99%) and ee value...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-04, Vol.76 (7), p.2282-2285
Main Authors: Wen, Lele, Shen, Qilong, Wan, Xiaolong, Lu, Long
Format: Article
Language:English
Subjects:
Alkylation
Carbon - chemistry
Catalysis
Chemistry
Copper - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Indoles - chemistry
Malonates - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:An enantioselective alkylation of indoles with trifluoroethylidene malonates catalyzed by copper(II)−bis (oxazoline) complexes has been developed. The expected adducts with a stereogenic tertiary carbon center bearing a trifluoromethyl group were obtained in excellent yields (up to 99%) and ee values (up to 96% ee). The synthetic utility of this asymmetric catalytic reaction was demonstrated by the preparation of β-CF3-tryptophan and 4-CF3-β-carboline in high ee.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo1024333