Organocatalytic Enantioselective Friedel−Crafts Reaction of Pyrrole Derivatives with Imines
Organic LettersPublished 30 August 2007
Guilong Li, Gerald B. Rowland, Emily B. Rowland, Jon C. Antilla
Citations152
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.
TL;DR
A highly enantioselective Friedel-Crafts reaction of pyrrole derivatives with N-acyl imines catalyzed by chiral phosphoric acids was developed and produced the pyr role derivatives in high yields and enantiOSElectivity.
Abstract
A highly enantioselective Friedel-Crafts reaction of pyrrole derivatives with N-acyl imines catalyzed by chiral phosphoric acids was developed. The reactions produced the pyrrole derivatives in high yields and enantioselectivity.
Keywords
Chemistry
Angewandte Chemie International EditionEnantioselective Mannich‐Type Reaction Catalyzed by a Chiral Brønsted Acid
1,641 Citations2004Takahiko Akiyama, Junji Itoh +2 more
Advanced Synthesis & CatalysisRecent Progress in Chiral Brønsted Acid Catalysis
888 Citations2006Takahiko Akiyama, Junji Itoh +1 more
Journal of the American Chemical SocietyEnantioselective Organocatalytic Reductive Amination
731 Citations2005Richard Storer, Diane E. Carrera +2 more
This new protocol realizes a key benefit of reductive amination versus imine reduction, in that ketimines derived from alkyl-alkyl ketones are unstable to isolation, a fundamental limitation that is comprehensively bypassed using this direct organocatalytic reductiveAmination.
Angewandte Chemie International EditionA Highly Enantioselective Brønsted Acid Catalyzed Cascade Reaction: Organocatalytic Transfer Hydrogenation of Quinolines and their Application in the Synthesis of Alkaloids
724 Citations2006Magnus Rueping, Andrey P. Antonchick +1 more
The recently developed biomimetic, enantioselective Brønsted acid catalyzed transfer hydrogenation of imines is wondered whether it would be possible to extend to the enantiOSElective processes.
Angewandte Chemie International EditionA Powerful Brønsted Acid Catalyst for the Organocatalytic Asymmetric Transfer Hydrogenation of Imines
651 Citations2005S.D. Hoffmann, Abdul Majeed Seayad +1 more
Journal of the American Chemical SocietyNew Strategies in Organic Catalysis: The First Enantioselective Organocatalytic Friedel−Crafts Alkylation
573 Citations2001Nick A. Paras, David W. C. MacMillan
This work reveals that the LUMO-lowering activation of α,β-unsaturated aldehydes using the reversible formation of iminium ions with chiral imidazolidinones 1 is a valuable platform for the development of enantioselective organocatalytic Diels−Alder reactions.
Organic LettersEnantioselective Brønsted Acid Catalyzed Transfer Hydrogenation: Organocatalytic Reduction of Imines
490 Citations2005Magnus Rueping, Erli Sugiono +3 more
The first enantioselective Brønsted acid catalyzed reduction of imines has been developed and this new organocatalytic transfer hydrogenation of ketimines with Hantzsch dihydropyridine as the hydrogen source offers a mild method to various chiral amines with high enantiOSElectivity.
Journal of the American Chemical SocietyChiral Brønsted Acid-Catalyzed Inverse Electron-Demand Aza Diels−Alder Reaction
390 Citations2006Takahiko Akiyama, Hisashi Morita +1 more
Inverse electron-demand aza Diels-Alder reaction of aldimine with enol ethers proceeded under the influence of a phosphoric acid diester, derived from (R)-BINOL, to give tetrahydroquinoline derivatives with excellent enantioselectivity.
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 SocietyBrønsted Acid-Catalyzed Imine Amidation
305 Citations2005Gerald B. Rowland, Haile Zhang +4 more
A new method for the Brønsted acid-catalyzed addition of amide nucleophiles to imines to produce protected aminal products is described.
Angewandte Chemie International EditionRemarkably Low Catalyst Loading in Brønsted Acid Catalyzed Transfer Hydrogenations: Enantioselective Reduction of Benzoxazines, Benzothiazines, and Benzoxazinones
304 Citations2006Magnus Rueping, Andrey P. Antonchick +1 more
Journal of the American Chemical SocietyA Vaulted Biaryl Phosphoric Acid-Catalyzed Reduction of α-Imino Esters: The Highly Enantioselective Preparation of α-Amino Esters
303 Citations2007Guilong Li, Yuxue Liang +1 more
It was shown that imino substrates derived from substituted aryl and alkyl keto esters could be reduced to the corresponding α-amino ester in excellent yield and in enantiomeric excesses from 94 to 99%.
Organic LettersChiral Brønsted Acid Catalyzed Enantioselective Hydrophosphonylation of Imines: Asymmetric Synthesis of α-Amino Phosphonates
289 Citations2005Takahiko Akiyama, Hisashi Morita +2 more
A cyclic phosphoric acid derivative, derived from (R)-BINOL, was used as a chiral Bronsted acid in hydrophosphonylation of aldimines with diisopropyl phosphite at room temperature with good to high enantioselectivities.
Angewandte ChemieHigh Substrate/Catalyst Organocatalysis by a Chiral Brønsted Acid for an Enantioselective Aza‐Ene‐Type Reaction
242 Citations2006Masahiro Terada, Kyoko Machioka +1 more
Elsevier eBooksFriedel–Crafts Alkylations
224 Citations1991George A. Olah, Ramesh Krishnamurti +1 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.
Angewandte Chemie International EditionA Highly Enantioselective Brønsted Acid Catalyst for the Strecker Reaction
210 Citations2006Magnus Rueping, Erli Sugiono +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.
Organic LettersThe Highly Enantioselective Addition of Indoles to <i>N</i>-Acyl Imines with Use of a Chiral Phosphoric Acid Catalyst
190 Citations2007Gerald B. Rowland, Emily B. Rowland +3 more
The highly enantioselective organocatalytic addition of N-benzyl indoles to N-acyl imines is reported and attractive features of the reaction include desirable catalyst loadings, good reactivity, generality of substrates, and easily removable groups from both nitrogen atoms.
Angewandte Chemie International EditionCooperative Coexistence: Effective Interplay of Two Brønsted Acids in the Asymmetric Synthesis of Isoquinuclidines
184 Citations2006Magnus Rueping, Cengiz Azap
Organic LettersCatalytic Enantioselective Pyrrole Alkylations of α,β-Unsaturated 2-Acyl Imidazoles
151 Citations2006David A. Evans, Keith R. Fandrick
A short, enantioselective synthesis of the alkaloid (+)-heliotridane has been accomplished utilizing this methodology and a 2-acyl imidazole cleavage and cyclization and was extended to the one-pot asymmetric synthesis of 2-substituted indoles.
Journal of Medicinal ChemistryAbsolute configuration of (-)-5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid, the active enantiomer of ketorolac
84 Citations1986Angel Gusman, Francisco Yuste +2 more
The (-)-S isomer of 5-benzoyl-1, 2-dihydro-3H-pyrrolo[1,2-alpha]pyrrole-1-carboxylic acid is about 60 times more potent than the (+)-R isomer in the carrageenan edema test and 230 times more active in the mouse phenylquinone writhing assay.
The Journal of Organic ChemistryNovel Routes to 1,2,3,4-Tetrahydropyrrolo[1,2-<i>a</i>]pyrazines and 5,6,9,10,11,11a-Hexahydro-8<i>H</i>-pyrido[1,2-<i>a</i>]pyrrolo[2,1-<i>c</i>]pyrazines
22 Citations2002Alan R. Katritzky, Ritu Jain +2 more
