Asymmetric Friedel−Crafts Addition of Indoles to <i>N</i>-Sulfonyl Aldimines: A Simple Approach to Optically Active 3-Indolyl-methanamine Derivatives
Organic LettersPublished 16 March 2006
Yi‐Xia Jia, Jian‐Hua Xie, Haifeng Duan, Lixin Wang, Qi‐Lin Zhou
Citations167
SJR quartileQ1
SJR score1.24
SNIP1.03
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
Abstract
[reaction: see text] The enantioselective copper(II)-catalyzed Friedel-Crafts addition of indoles to N-sulfonyl aldimines was developed using chiral bisoxazoline as ligands, and high enantioselectivities (up to 96% ee) were achieved.
Keywords
Chemistry
Elsevier eBooksComprehensive organic synthesis
6,249 Citations2014Paul Knochel, Gary A. Molander
Synthetic chemists requiring the essential facts in new areas, as well as students completely new to the field, will find "Comprehensive Organic Synthesis, Second Edition" an invaluable source, providing an authoritative overview of core concepts.
Journal of the American Chemical SocietyOrganocatalytic Asymmetric Aza-Friedel−Crafts Alkylation of Furan
353 Citations2004Daisuke Uraguchi, Keiichi Sorimachi +1 more
The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion and could be further derivatized to a chiral gamma-butenolid.
Journal of the American Chemical SocietyEnantioselective Friedel−Crafts Alkylations of α,β-Unsaturated 2-Acyl Imidazoles Catalyzed by Bis(oxazolinyl)pyridine−Scandium(III) Triflate Complexes
304 Citations2005David A. Evans, Keith R. Fandrick +1 more
Journal of the American Chemical SocietySidearm Effect: Improvement of the Enantiomeric Excess in the Asymmetric Michael Addition of Indoles to Alkylidene Malonates
270 Citations2002Jian Zhou, Yong Tang
A pseudo-C3-trisoxazoline was designed and synthesized by a sidearm approach that resulted in highly catalytic enantioselective Michael addition of indoles to alkylidene malonates.
Angewandte Chemie International EditionCatalytic Asymmetric Friedel-Crafts Alkylation of β,γ-Unsaturated α-Ketoesters: Enantioselective Addition of Aromatic C−H Bonds to Alkenes
235 Citations2001Kim B. Jensen, Jacob Thorhauge +2 more
Angewandte Chemie International EditionA Copper(<scp>II</scp>)‐Catalyzed Aza‐Friedel–Crafts Reaction of <i>N</i>‐(2‐Pyridyl)sulfonyl Aldimines: Synthesis of Unsymmetrical Diaryl Amines and Triaryl Methanes
232 Citations2005Jorge Esquivias, Ramón Goméz Arrayás +1 more
PubMedCatalytic Asymmetric Friedel-Crafts Alkylation of beta,gamma-Unsaturated alpha-Ketoesters: Enantioselective Addition of Aromatic C-H Bonds to Alkenes This work was made possible by a grant from the Danish National Research Foundation.
225 Citations2001Kim B. Jensen, Jacob Thorhauge +2 more
Journal of the American Chemical SocietyEnantioselective Indole Friedel−Crafts Alkylations Catalyzed by Bis(oxazolinyl)pyridine−Scandium(III) Triflate Complexes
219 Citations2003David A. Evans, Karl A. Scheidt +3 more
A highly enantioselective Friedel-Crafts alkylation of electron-rich aromatic nucleophiles catalyzed by scandium(III) triflate-pyridyl(bis)oxazoline complexes has been accomplished.
The Journal of Organic ChemistryAsymmetric Friedel−Crafts Alkylations of Indoles with Nitroalkenes Catalyzed by Zn(II)−Bisoxazoline Complexes
212 Citations2005Yi‐Xia Jia, Shuo‐Fei Zhu +2 more
Journal of the American Chemical SocietyHighly Enantioselective Friedel−Crafts Alkylations of Pyrroles and Indoles with α‘-Hydroxy Enones under Cu(II)-Simple Bis(oxazoline) Catalysis
211 Citations2005Claudio Palomo, Mikel Oiarbide +3 more
Remarkably high and regular enantioselectivities are obtained in Friedel-Crafts alkylation reactions involving alpha'-hydroxy enone templates and Cu(II)-bis(oxazoline) complexes as catalysts.
Tetrahedron LettersDy(OTf)3 in ionic liquid: an efficient catalytic system for reactions of indole with aldehydes/ketones or imines
198 Citations2004Xueling Mi, Sanzhong Luo +2 more
Journal of the American Chemical SocietyCatalytic Enantioselective Friedel−Crafts Reactions of Aromatic Compounds with Glyoxylate: A Simple Procedure for the Synthesis of Optically Active Aromatic Mandelic Acid Esters
197 Citations2000Nicholas Gathergood, Wei Zhuang +1 more
The Journal of Organic ChemistryCatalytic, Highly Enantioselective Friedel−Crafts Reactions of Aromatic and Heteroaromatic Compounds to Trifluoropyruvate. A Simple Approach for the Formation of Optically Active Aromatic and Heteroaromatic Hydroxy Trifluoromethyl Esters
191 Citations2001Wei Zhuang, Nicholas Gathergood +2 more
A new catalytic enantioselective synthetic method for the formation of optically active aromatic and heteroaromatic hydroxy-trifluoromethyl ethyl esters is presented, which proceeds in good yield and with high enantiomeric excess.
Chemical CommunicationsAn enantioselective synthesis of heteroaromatic N-tosyl α-amino acids
137 Citations1999Mogens Johannsen
A new synthesis of optically active β-indolyl and pyrrolyl N-tosyl α-amino acids has been developed which uses readily available starting materials and proceeds with a high degree of enantioselection, giving up to 96% enantiomeric purity in 89% yield using 1–5 mol% of a chiral copper(I)–Tol-BINAP catalyst.
Angewandte Chemie International EditionKinetic Resolution of Epoxides by a CC Bond‐Forming Reaction: Highly Enantioselective Addition of Indoles to <i>cis</i>, <i>trans</i>, and <i>meso</i> Aromatic Epoxides Catalyzed by [Cr(salen)] Complexes
124 Citations2003Marco Bandini, Pier Giorgio Cozzi +2 more
Angewandte Chemie International Edition in EnglishEnantioselective Catalysis with a New Zirconium Trichloride Lewis Acid Containing a “Dibornacyclopentadienyl” Ligand
114 Citations1990Gerhard Erker, A. A. H. VAN DER ZEIJDEN
Angewandte Chemie International EditionFormation of Optically Active Aromaticα-Amino Acids by Catalytic Enantioselective Addition of Imines to Aromatic Compounds
110 Citations2000Steen Saaby, Xiangming Fang +2 more
Organic LettersEnantioselective Friedel−Crafts Alkylation Reactions Catalyzed by a Chiral Nonracemic <i>C</i><sub>2</sub>-Symmetric 2,2‘-Bipyridyl Copper(II) Complex
109 Citations2005Michael P. A. Lyle, N.D. Draper +1 more
The Journal of Organic ChemistryAsymmetric Catalysis of the Friedel−Crafts Reaction with Fluoral by Chiral Binaphthol-Derived Titanium Catalysts through Asymmetric Activation
105 Citations2000Akihiro Ishii, Vadim A. Soloshonok +1 more
The Journal of Organic ChemistryOptically Active Aromatic and Heteroaromatic α-Amino Acids by a One-Pot Catalytic Enantioselective Addition of Aromatic and Heteroaromatic C−H Bonds to α-Imino Esters
92 Citations2002Steen Saaby, Pau Bayón +2 more
The development of a practical one-pot catalytic enantioselective procedure for the synthesis of non-natural aromatic and heteroaromatic alpha-amino acids is reported.
Chemical CommunicationsA highly efficient gold/silver-catalyzed addition of arenes to imines
66 Citations2004Yumei Luo, Chao‐Jun Li
A highly efficient imino Friedel-Crafts type addition of arenes to imines is developed by using a combination of gold and silver catalysts; various amino acid derivatives are generated by this method.
SynlettLanthanide Triflates Catalyzed Reactions of Imines with Indole in Protic Media
49 Citations1999Wenhua Xie, Karen M. Bloomfield +3 more
The Journal of Organic ChemistrySynthesis of 3-[(1-Aryl)aminomethyl]indoles
43 Citations2002James H. Wynne, Wayne M. Stalick
TetrahedronRegiospecific preparation of γ-carbolines andpyrimido[3, 4-a]indole derivatives by intramolecular ring-closure of heterocumulene-substituted indoles
30 Citations1996Pedro Molina, Julia ́n Alca ́ntara +1 more
