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Highly efficient asymmetric synthesis of 3-indolyl(hydroxy)acetates via Friedel-Crafts alkylation of indoles.
J Org Chem. 2009 Sep 04; 74(17):6878-80.JO

Abstract

An efficient enantioselective Friedel-Crafts alkylation of indoles to ethyl glyoxylate catalyzed by chiral N,N'-dioxide-Sc(III) complex was developed. The corresponding 3-indolyl(hydroxy)acetates compounds were afforded in good yields with high enantioselectivities (up to 95% ee).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Hui Y
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.
Zhang Q
No affiliation info available
Jiang J
No affiliation info available
Lin L
No affiliation info available
Liu X
No affiliation info available
Feng X
No affiliation info available

MeSH

AcetatesAlkylationCatalysisChemistry, PharmaceuticalDrug DesignGlyoxylatesIndolesLigandsMetalsModels, ChemicalOxidesSolventsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19658388

Citation

Hui, Yonghai, et al. "Highly Efficient Asymmetric Synthesis of 3-indolyl(hydroxy)acetates Via Friedel-Crafts Alkylation of Indoles." The Journal of Organic Chemistry, vol. 74, no. 17, 2009, pp. 6878-80.
Hui Y, Zhang Q, Jiang J, et al. Highly efficient asymmetric synthesis of 3-indolyl(hydroxy)acetates via Friedel-Crafts alkylation of indoles. J Org Chem. 2009;74(17):6878-80.
Hui, Y., Zhang, Q., Jiang, J., Lin, L., Liu, X., & Feng, X. (2009). Highly efficient asymmetric synthesis of 3-indolyl(hydroxy)acetates via Friedel-Crafts alkylation of indoles. The Journal of Organic Chemistry, 74(17), 6878-80. https://doi.org/10.1021/jo901425z
Hui Y, et al. Highly Efficient Asymmetric Synthesis of 3-indolyl(hydroxy)acetates Via Friedel-Crafts Alkylation of Indoles. J Org Chem. 2009 Sep 4;74(17):6878-80. PubMed PMID: 19658388.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly efficient asymmetric synthesis of 3-indolyl(hydroxy)acetates via Friedel-Crafts alkylation of indoles. AU - Hui,Yonghai, AU - Zhang,Qi, AU - Jiang,Jun, AU - Lin,Lili, AU - Liu,Xiaohua, AU - Feng,Xiaoming, PY - 2009/8/8/entrez PY - 2009/8/8/pubmed PY - 2009/12/22/medline SP - 6878 EP - 80 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 17 N2 - An efficient enantioselective Friedel-Crafts alkylation of indoles to ethyl glyoxylate catalyzed by chiral N,N'-dioxide-Sc(III) complex was developed. The corresponding 3-indolyl(hydroxy)acetates compounds were afforded in good yields with high enantioselectivities (up to 95% ee). SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19658388/Highly_efficient_asymmetric_synthesis_of_3_indolyl_hydroxy_acetates_via_Friedel_Crafts_alkylation_of_indoles_ DB - PRIME DP - Unbound Medicine ER -