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Enantioselective Friedel-Crafts alkylation of indoles with alkylidene malonates catalyzed by N,N'-dioxide-scandium(III) complexes: asymmetric synthesis of beta-carbolines.
Chemistry. 2009; 15(9):2055-8.C

Abstract

An efficient catalytic asymmetric Friedel-Crafts alkylation of indoles with alkylidene malonates has been developed by using a chiral N,N'-dioxide-Sc(OTf)(3) complex as the catalyst (see scheme). Some optically active intermediates containing the indole skeleton have been synthesized, such as indolepropionic acid, tryptamines, and beta-carbolines. The coordination between the scandium atom and the chiral N,N'-dioxide compound has been revealed by X-ray structure analysis.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Liu Y
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, China.
Shang D
No affiliation info available
Zhou X
No affiliation info available
Liu X
No affiliation info available
Feng X
No affiliation info available

MeSH

AlkylationCatalysisCrystallography, X-RayIndolesMalonatesMolecular ConformationMolecular StructureScandiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19177478

Citation

Liu, Yanling, et al. "Enantioselective Friedel-Crafts Alkylation of Indoles With Alkylidene Malonates Catalyzed By N,N'-dioxide-scandium(III) Complexes: Asymmetric Synthesis of Beta-carbolines." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 15, no. 9, 2009, pp. 2055-8.
Liu Y, Shang D, Zhou X, et al. Enantioselective Friedel-Crafts alkylation of indoles with alkylidene malonates catalyzed by N,N'-dioxide-scandium(III) complexes: asymmetric synthesis of beta-carbolines. Chemistry. 2009;15(9):2055-8.
Liu, Y., Shang, D., Zhou, X., Liu, X., & Feng, X. (2009). Enantioselective Friedel-Crafts alkylation of indoles with alkylidene malonates catalyzed by N,N'-dioxide-scandium(III) complexes: asymmetric synthesis of beta-carbolines. Chemistry (Weinheim an Der Bergstrasse, Germany), 15(9), 2055-8. https://doi.org/10.1002/chem.200802210
Liu Y, et al. Enantioselective Friedel-Crafts Alkylation of Indoles With Alkylidene Malonates Catalyzed By N,N'-dioxide-scandium(III) Complexes: Asymmetric Synthesis of Beta-carbolines. Chemistry. 2009;15(9):2055-8. PubMed PMID: 19177478.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Friedel-Crafts alkylation of indoles with alkylidene malonates catalyzed by N,N'-dioxide-scandium(III) complexes: asymmetric synthesis of beta-carbolines. AU - Liu,Yanling, AU - Shang,Deju, AU - Zhou,Xin, AU - Liu,Xiaohua, AU - Feng,Xiaoming, PY - 2009/1/30/entrez PY - 2009/1/30/pubmed PY - 2009/3/19/medline SP - 2055 EP - 8 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 15 IS - 9 N2 - An efficient catalytic asymmetric Friedel-Crafts alkylation of indoles with alkylidene malonates has been developed by using a chiral N,N'-dioxide-Sc(OTf)(3) complex as the catalyst (see scheme). Some optically active intermediates containing the indole skeleton have been synthesized, such as indolepropionic acid, tryptamines, and beta-carbolines. The coordination between the scandium atom and the chiral N,N'-dioxide compound has been revealed by X-ray structure analysis. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/19177478/Enantioselective_Friedel_Crafts_alkylation_of_indoles_with_alkylidene_malonates_catalyzed_by_NN'_dioxide_scandium_III__complexes:_asymmetric_synthesis_of_beta_carbolines_ L2 - https://doi.org/10.1002/chem.200802210 DB - PRIME DP - Unbound Medicine ER -
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