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Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles.
Org Lett. 2008 Mar 06; 10(5):933-5.OL

Abstract

A simple and efficient synthesis to both enantiomers of highly enantiomerically enriched alpha-trifluoromethyl-alpha-(heteroaryl)-glycine derivatives via highly stereoselective aminoalkylation of indoles and pyrroles is described. The triflic acid-catalyzed reaction of enantiomeric 3,3,3-trifluoro-pyruvate-alpha-methylbenzyl imines with indoles and pyrroles and the subsequent Pd-catalyzed hydrogenolysis of the methylbenzyl group provided the products in high yields and excellent enantioselectivities.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Abid M
Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd. Boston, Massachusetts 02125-3393, USA.
Teixeira L
No affiliation info available
Török B
No affiliation info available

MeSH

AlkylationAminesCatalysisGlycineHydrocarbons, FluorinatedIndolesMesylatesMolecular StructurePyrrolesStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18254637

Citation

Abid, Mohammed, et al. "Triflic Acid-catalyzed Highly Stereoselective Friedel-crafts Aminoalkylation of Indoles and Pyrroles." Organic Letters, vol. 10, no. 5, 2008, pp. 933-5.
Abid M, Teixeira L, Török B. Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles. Org Lett. 2008;10(5):933-5.
Abid, M., Teixeira, L., & Török, B. (2008). Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles. Organic Letters, 10(5), 933-5. https://doi.org/10.1021/ol703095d
Abid M, Teixeira L, Török B. Triflic Acid-catalyzed Highly Stereoselective Friedel-crafts Aminoalkylation of Indoles and Pyrroles. Org Lett. 2008 Mar 6;10(5):933-5. PubMed PMID: 18254637.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles. AU - Abid,Mohammed, AU - Teixeira,Liliana, AU - Török,Béla, Y1 - 2008/02/07/ PY - 2008/2/8/pubmed PY - 2008/5/16/medline PY - 2008/2/8/entrez SP - 933 EP - 5 JF - Organic letters JO - Org Lett VL - 10 IS - 5 N2 - A simple and efficient synthesis to both enantiomers of highly enantiomerically enriched alpha-trifluoromethyl-alpha-(heteroaryl)-glycine derivatives via highly stereoselective aminoalkylation of indoles and pyrroles is described. The triflic acid-catalyzed reaction of enantiomeric 3,3,3-trifluoro-pyruvate-alpha-methylbenzyl imines with indoles and pyrroles and the subsequent Pd-catalyzed hydrogenolysis of the methylbenzyl group provided the products in high yields and excellent enantioselectivities. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/18254637/Triflic_acid_catalyzed_highly_stereoselective_friedel_crafts_aminoalkylation_of_indoles_and_pyrroles_ DB - PRIME DP - Unbound Medicine ER -