Highly diastereoselective synthesis of arylglycine derivatives via TFA-promoted Friedel–Crafts reactions of phenols with cyclic glyoxylate imines
TetrahedronPublished 1 September 2003
Xiaopeng Cheng, Fei Lei, Li Liu, Dong Wang
Citations29
SJR quartileQ3
SJR score0.43
SNIP0.60
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
Optically active α-arylglycine derivatives were synthesized by Brønsted acid (TFA)-promoted Friedel–Crafts reaction of various phenols with chiral cyclic glyoxylate imines (2a–c), followed by deprotection with Pd(OH)2/C under H2. The diastereoselectivities of the initially formed F–C reaction products are up to 99%.
Keywords
ChemistryBiochemistry, Genetics and Molecular BiologyPharmacology, Toxicology and Pharmaceutics
TetrahedronRecent developments in the stereoselective synthesis of α-aminoacids
792 Citations1994Rudolf O. Duthaler
Journal of Medicinal ChemistryLigands for Glutamate Receptors: Design and Therapeutic Prospects
525 Citations2000Hans Bräuner‐Osborne, Jan Egebjerg +3 more
Angewandte Chemie International EditionVancomycin Assembly: Nature's Way
353 Citations2003Brian K. Hubbard, Christopher T. Walsh
The rules by which nature assembles the glycopeptid (vancomycin) and lipoglycopeptide (teicoplanin) antibiotics are becoming elucidated and verified: first amino acids are synthesized, then joined together and cross-linked.
Chemical ReviewsAsymmetric synthesis of arylglycines
337 Citations1992Robert M. Williams, James A. Hendrix
Organic LettersEnantioselective Catalytic Addition of HCN to Ketoimines. Catalytic Synthesis of Quaternary Amino Acids
299 Citations2000Petr Váchal, Eric N. Jacobsen
Qu quantitative isolated yield and enantioselectivity of up to 95% ee was obtained and some of the Strecker adducts could be recrystallized in high recovery, yielding optically pure materials.
Journal of the American Chemical SocietyChiral Magnesium Bis(sulfonamide) Complexes as Catalysts for the Merged Enolization and Enantioselective Amination of <i>N</i>-Acyloxazolidinones. A Catalytic Approach to the Synthesis of Arylglycines
251 Citations1997David A. Evans, Scott G. Nelson
Journal of the American Chemical SocietyTi-Catalyzed Enantioselective Addition of Cyanide to Imines. A Practical Synthesis of Optically Pure α-Amino Acids
235 Citations1999Clinton A. Krueger, Kevin W. Kuntz +5 more
Journal of the American Chemical SocietyAsymmetric synthesis of R and S .alpha.-alkylalkanoic acids from metalation and alkylation of chiral 2-oxazolines
190 Citations1976A. I. MEYERS, Gerald Knaus +2 more
The Journal of Organic ChemistrySynthesis of optically pure .alpha.-alkylated .alpha.-amino acids and a single-step method for enantiomeric excess determination
148 Citations1988W. Kruizinga, John Bolster +5 more
Angewandte Chemie International Edition in EnglishSmaller Substituents on Nitrogen Facilitate the Osmium‐Catalyzed Asymmetric Aminohydroxylation
145 Citations1996Joachim Rudolph, Peter Sennhenn +2 more
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.
Tetrahedron LettersAsymmetric synthesis of α-amino acids and α-N-hydroxyamino acids via electrophilic amination of bornanesultam-derived enolates with 1-chloro-1-nitrosocyclohexane.
127 Citations1990Wolfgang Oppolzer, Osamu Tamura
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
Tetrahedron LettersA general approach to the asymmetric synthesis of vancomycin-related arylglycines by enolate azidation
101 Citations1992David A. Evans, Deborah A. Evrad +4 more
The Journal of Organic ChemistryChemoenzymic synthesis of chiral furan derivatives: useful building blocks for optically active structures
90 Citations1988Dale G. Drueckhammer, Carlos F. Barbas +4 more
TetrahedronEt3B- and Et2Zn-Mediated Radical Additions to Glyoxylate Imines, Compared Stereoinductions
79 Citations2000Michèle P. Bertrand, Stéphanie Coantic +3 more
Synlett1,3-Stereoinduction in Radical Additions to Glyoxylate Imines
67 Citations1998Michèle P. Bertrand, Laurence Feray +2 more
Journal of the American Chemical SocietyThe Synthesis of the 2-Amino-3-(3-indolyl)-butyric Acids (β-Methyltryptophans)
66 Citations1957H. R. Snyder, Donald S. Matteson
SynlettCarbon-Carbon Bond Forming Reactions by using Bistrifluoromethanesulfonimide
51 Citations2002Janine Cossy, François Lutz +2 more
The Journal of Organic ChemistryAsymmetric synthesis of arylglycines
49 Citations1990Robert M. Williams, James A. Hendrix
Chemical CommunicationsNovel intermolecular carbon radical addition to a nitrone: asymmetric synthesis of α-amino acidsElectronic supplementary information (ESI) available: experimental procedures. See http://www.rsc.org/suppdata/cc/b2/b211570k/
46 Citations2003Masafumi Ueda, Hideto Miyabe +3 more
The Journal of Organic ChemistrySynthesis of (<i>S</i>)-α-Cyclopropyl-4- phosphonophenylglycine
42 Citations2000Dawei Ma, Wei Zhu
Tetrahedron LettersSynthesis of amino acids via a three-component reaction of phenols, glyoxylates and amines
42 Citations2000Taisheng Huang, Chao‐Jun Li
The Journal of Organic ChemistryOxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2<i>H</i>-1,4-oxazin-2-ones and Morpholin-2-ones
41 Citations1996Cynthia M. Shafer, Tadeusz F. Molinski
PubMedNovel intermolecular carbon radical addition to a nitrone: asymmetric synthesis of alpha-amino acids.
39 Citations2003Masafumi Ueda, Hideto Miyabe +3 more
A Nitrone was used as a synthetically useful radical acceptor in carbon-carbon bond-forming radical reactions and a high degree of stereocontrol in radical addition to glyoxylic nitrone was achieved to provide a new method for asymmetric synthesis of alpha-amino acids.
Expert Opinion on Therapeutic PatentsRecent developments in reversing glycopeptide-resistant pathogens
33 Citations1999Jieping Zhu
Biosearch Italia SpA worked on new synthetic glycopeptides with a modified binding pocket in order to find drugs active against both vancomycin-sensitive and -resistant strains and a new mechanistic proposal that can account for the bioactivity of LY 333328 against VRE was summarised.
Tetrahedron AsymmetryA practical asymmetric synthesis of homochiral α-arylglycines
31 Citations2001Christelle Mellin-Morlière, David J. Aitken +3 more
Journal of the Chemical Society Perkin Transactions 1Ene reaction of the active imino group. A novel synthesis of α-amino-acids
25 Citations1981O. Achmatowicz, Marek Pietraszkiewicz
Tetrahedron AsymmetryAsymmetric synthesis of (S)-1-aminoindan-1,5-dicarboxylic acid and related analogues via intramolecular acylation of enantiopure α,α-disubstituted amino acids
19 Citations2002Dawei Ma, Ke Ding +3 more
SynlettHighly Diastereoselective Synthesis of N-Protected Arylglycine Derivatives via TiCl4-Promoted Friedel-Crafts Reaction of Phenols with Chiral N,O-Hemiacetal
17 Citations2002Chengsheng Ge, Xiaopeng Cheng +1 more
Tetrahedron AsymmetrySynthesis of enantiomerically pure α-amino acids via chemo- and diastereoselective alkylation of (5S)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one
15 Citations1997Laurence M. Harwood, Simon N. G. Tyler +3 more
Bulletin of the Chemical Society of JapanThe Optical Resolution and Asymmetric Transformation of <scp>Dl</scp>-<i>p</i>-Hydroxyphenylglycine with (+)-1-Phenylethanesulfonic Acid
15 Citations1987Ryuzo Yoshioka, Masanori Tohyama +3 more
SynlettSynthesis of Optically Active α-Arylglycines: Stereoselective Mannich-Type Reaction with a New Chiral Template
14 Citations2001Shigemitsu Tohma, Atsushi Endo +2 more
SynlettAn Acetone-derived Chiral Stabilised Azomethine Ylid: Synthesis of Enantiomerically Pure 5,5,-Dimethylproline Derivatives
7 Citations2001David Aldous, Michael G. B. Drew +4 more