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Enantioselective Friedel-Crafts alkylation of indoles with trifluoroethylidene malonates by copper-bis(oxazoline) complexes: construction of trifluoromethyl-substituted stereogenic tertiary carbon center.
J Org Chem. 2011 Apr 01; 76(7):2282-5.JO

Abstract

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-CF(3)-tryptophan and 4-CF(3)-β-carboline in high ee.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Wen L
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Rd., Shanghai, 200032, China.
Shen Q
No affiliation info available
Wan X
No affiliation info available
Lu L
No affiliation info available

MeSH

AlkylationCarbonCatalysisCopperHydrocarbons, FluorinatedIndolesMalonatesMolecular StructureStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21375277

Citation

Wen, Lele, et al. "Enantioselective Friedel-Crafts Alkylation of Indoles With Trifluoroethylidene Malonates By Copper-bis(oxazoline) Complexes: Construction of Trifluoromethyl-substituted Stereogenic Tertiary Carbon Center." The Journal of Organic Chemistry, vol. 76, no. 7, 2011, pp. 2282-5.
Wen L, Shen Q, Wan X, et al. Enantioselective Friedel-Crafts alkylation of indoles with trifluoroethylidene malonates by copper-bis(oxazoline) complexes: construction of trifluoromethyl-substituted stereogenic tertiary carbon center. J Org Chem. 2011;76(7):2282-5.
Wen, L., Shen, Q., Wan, X., & Lu, L. (2011). Enantioselective Friedel-Crafts alkylation of indoles with trifluoroethylidene malonates by copper-bis(oxazoline) complexes: construction of trifluoromethyl-substituted stereogenic tertiary carbon center. The Journal of Organic Chemistry, 76(7), 2282-5. https://doi.org/10.1021/jo1024333
Wen L, et al. Enantioselective Friedel-Crafts Alkylation of Indoles With Trifluoroethylidene Malonates By Copper-bis(oxazoline) Complexes: Construction of Trifluoromethyl-substituted Stereogenic Tertiary Carbon Center. J Org Chem. 2011 Apr 1;76(7):2282-5. PubMed PMID: 21375277.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Friedel-Crafts alkylation of indoles with trifluoroethylidene malonates by copper-bis(oxazoline) complexes: construction of trifluoromethyl-substituted stereogenic tertiary carbon center. AU - Wen,Lele, AU - Shen,Qilong, AU - Wan,Xiaolong, AU - Lu,Long, Y1 - 2011/03/04/ PY - 2011/3/8/entrez PY - 2011/3/8/pubmed PY - 2011/9/29/medline SP - 2282 EP - 5 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 7 N2 - 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-CF(3)-tryptophan and 4-CF(3)-β-carboline in high ee. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21375277/Enantioselective_Friedel_Crafts_alkylation_of_indoles_with_trifluoroethylidene_malonates_by_copper_bis_oxazoline__complexes:_construction_of_trifluoromethyl_substituted_stereogenic_tertiary_carbon_center_ L2 - https://doi.org/10.1021/jo1024333 DB - PRIME DP - Unbound Medicine ER -