Enantio‐ and Diastereoselective Ir‐Catalyzed Allylic Substitutions for Asymmetric Synthesis of Amino Acid Derivatives
Angewandte Chemie International EditionPublished 8 May 2003
Takatoshi Kanayama, Kazumasa Yoshida, Hideto Miyabe, Yoshiji Takemoto
Citations182
SJR quartileQ1
SJR score5.55
SNIP2.47
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
Simply switching the base employed in the first enantioselective allylic substitutions of diphenylimino glycinate 1 with 2, which are catalyzed by an Ir complex of chiral phosphite 5, allows the two branched diastereomers 3 and 4 to be selectively synthesized with little or no formation of linear substitution products.
Keywords
Chemistry
Accounts of Chemical ResearchPhosphinooxazolinesA New Class of Versatile, Modular P,N<i>-</i>Ligands for Asymmetric Catalysis
1,290 Citations2000Günter Helmchen, Andreas Pfaltz
Angewandte Chemie International EditionHighly Enantioselective Rh-Catalyzed Hydrogenation Reactions Based on Chiral Monophosphite Ligands
371 Citations2000Manfred T. Reetz, Gerlinde Mehler
Chemical and Pharmaceutical BulletinPd Asymmetric Allylic Alkylation (AAA). A Powerful Synthetic Tool.
315 Citations2002Barry M. Trost
A family of ligands derived from 2-diphenylphosphinobenzoic or 1-naphthoic acid and chiral scalemic diamines have been successful in inducing excellent enantioselectivity by five different enantiodiscriminating events.
Journal of the American Chemical SocietyHighly Regio- and Enantioselective Pd-Catalyzed Allylic Alkylation and Amination of Monosubstituted Allylic Acetates with Novel Ferrocene <i>P,N</i>-Ligands
310 Citations2001Shu‐Li You, Xia‐Zhen Zhu +3 more
Angewandte Chemie International EditionNew Ligands for Regio- and Enantiocontrol in Pd-Catalyzed Allylic Alkylations
285 Citations1998Roger Prétôt, Andreas Pfaltz
The branched, chiral products 1 are formed preferentially in the allylic alkylations in Equation (1) when the Pd catalyst contains the P,N ligand L* or derivatives thereof.
Tetrahedron LettersFirst Enantioselective Alkylations of Monosubstituted Allylic Acetates Catalyzed by Chiral Iridium Complexes
274 Citations1997Jörg. P. Janssen, Günter Helmchen
Organic LettersChiral Phosphine-Free Pd-Mediated Asymmetric Allylation of Prochiral Enolate with a Chiral Phase-Transfer Catalyst
230 Citations2001Masayoshi Nakoji, Takatoshi Kanayama +2 more
A chiral phase-transfer catalyst has been applied to the asymmetric allylation of the tert-butyl glycinate-benzophenone Schiff base with various allylic acetates for the first time to give the allylated products in good yields and with comparable to higher enantioselectivity than for asymmetric alkylation at the same temperature.
SynlettThe Ups and Downs of Allylpalladium Complexes in Catalysis
211 Citations1996Jonathan M. J. Williams
Angewandte Chemie International Edition in EnglishChiral Phosphanodihydrooxazoles in Asymmetric Catalysis: Tungsten‐Catalyzed Allylic Substitution
207 Citations1995Guy C. Lloyd‐Jones, Andreas Pfaltz
Journal of the American Chemical SocietyEnantioselective Allylations of Azlactones with Unsymmetrical Acyclic Allyl Esters
198 Citations1999Barry M. Trost, Xavier Ariza
Chemical CommunicationsIr-catalysed allylic substitution: mechanistic aspects and asymmetric synthesis with phosphorus amidites as ligands
197 Citations1999Björn Bartels, Günter Helmchen
Ir-catalysed allylic alkylations of enantiomerically enriched monosubstituted allylic acetates proceed with up to 79% retention of configuration using P(OPh)3 as ligand, further evidence supports the assumption of σ-allyl complexes as intermediates.
Journal of the American Chemical SocietySynthesis of Novel Quaternary Amino Acids Using Molybdenum-Catalyzed Asymmetric Allylic Alkylation
195 Citations2002Barry M. Trost, Kalindi Dogra
The Mo-catalyzed asymmetric allylic alkylation using azlactones provides extraordinary levels of selectivity and ready access to unusual quarternary amino acids, important building blocks for biological applications.
Asymmetric Carbon–Carbon Bond‐Forming Reactions: Asymmetric Allylic Alkylation Reactions
184 Citations2000Barry M. Trost, Chulbom Lee
Chemical Society ReviewsEnantioselective catalysis using phosphorus-donor ligands containing two or three P–N or P–O bonds
181 Citations2002Jeffrey R. Ansell, Martin Wills
This review describes some recent developments in the area of asymmetric catalysis using organometallic complexes of ligands which contain two or three P-O or P-N bonds, which demonstrate remarkably high enantioinduction properties in a series of asymmetrical transformations.
Tetrahedron AsymmetryPalladium-catalyzed allylic alkylation of tert-butyl(diphenylmethylene)-glycinate with simple allyl esters under chiral phase transfer conditions
180 Citations2001Guo‐Shu Chen, Yijian Deng +6 more
Journal of the American Chemical SocietyAsymmetric Catalysis of Planar-Chiral Cyclopentadienylruthenium Complexes in Allylic Amination and Alkylation
177 Citations2001Yuji Matsushima, Kiyotaka Onitsuka +3 more
Angewandte Chemie International Edition in EnglishCatalytic Asymmetric Alkylation of Nucleophiles: Asymmetric Synthesis of α‐Alkylated Amino Acids
157 Citations1997Barry M. Trost, Xavier Ariza
The Journal of Organic ChemistryPd-Catalyzed Asymmetric Allylic Alkylation of Glycine Imino Ester Using a Chiral Phase-Transfer Catalyst
140 Citations2002Masayoshi Nakoji, Takatoshi Kanayama +2 more
Pd-catalyzed asymmetric allylic alkylation of the glycine imino ester 1a has been developed using a chiral quaternary ammonium salt 3d without chiral phosphine ligands to achieve high enantioselectivity.
Journal of the American Chemical SocietyRegio- and Enantioselective Molybdenum-Catalyzed Alkylations of Polyenyl Esters
133 Citations1999Barry M. Trost, Stefan Hildbrand +1 more
The Journal of Organic ChemistryTheoretical studies in molecular recognition: asymmetric induction of benzophenone imine ester enolates by the benzylcinchoninium ion
130 Citations1991Kenny B. Lipkowitz, Michael W. Cavanaugh +2 more
Journal of the American Chemical SocietyCatalytic Asymmetric Allylation of Prochiral Nucleophiles, α-Acetamido-β-ketoesters
123 Citations1999Ryoichi Kuwano, Yoshihiko Ito
Journal of Organometallic ChemistryCatalytic asymmetric reactions via π-allylpalladium complexes coordinated with chiral monophosphine ligands
121 Citations1999Tamio Hayashi
TetrahedronRegiocontrol and Stereoselectivity in Tungsten-Bipyridine Catalysed Allylic Alkylation
120 Citations1995Jürg Lehmann, Guy C. Lloyd‐Jones
Angewandte Chemie International EditionDesigned Ligands as Probes for the Catalytic Binding Mode in Mo-Catalyzed Asymmetric Allylic Alkylation We thank the National Science Foundation and the National Institutes of Health for their generous support of the work carried out at Stanford. I.H. thanks the Japan Society for the Promotion of Science for a postdoctoral fellowship. Mass spectra were provided by the Mass Spectrometry Facility at the University of California, San Francisco, which is supported by the NIH Division of Research Resources.
113 Citations2002Barry M. Trost, Kalindi Dogra +8 more
Chemical CommunicationsNovel bis-N-[2-(diphenylphosphino)ferrocenylcarbonyl]diaminocyclohexane ligands: application in asymmetric allylic alkylation of imino esters with simple allyl carbonate
111 Citations2000Shu‐Li You, Xue‐Long Hou +3 more
TetrahedronSynthesis of α-amino acids using transition metal catalysis - alkylation of schiff bases derived from α-amimo acid esters (regio, stereo - selectivity)
106 Citations1988J.‐P. GENET, Sylvain Jugé +4 more
Angewandte Chemie International EditionFast, Convenient, and Efficient Molybdenum-Catalyzed Asymmetric Allylic Alkylation under Noninert Conditions: An Example of Microwave-Promoted Fast Chemistry
105 Citations2000Nils‐Fredrik K. Kaiser, Ulf Bremberg +3 more
Angewandte ChemieHoch enantioselektive Rh-katalysierte Hydrierungen unter Verwendung von chiralen Monophosphit-Liganden
95 Citations2000Manfred T. Reetz, Gerlinde Mehler
Angewandte Chemie International EditionChelated Enolates of Amino Acid Esters—Efficient Nucleophiles in Palladium-Catalyzed Allylic Substitutions
88 Citations1999Uli Kazmaier, Franz L. Zumpe
This palladium-catalyzed reaction proceeds under very mild conditions and is suitable for the synthesis of enantiomerically pure amino acids (see reaction scheme).
OrganometallicsChiral Phosphito−Thioether Complexes of Palladium(0). Comments on the Pd, Rh, and Ir Regio- and-Enantioselective Allylic Alkylations of PhCHCHCH(OAc)R, R = H, Me, Et
87 Citations1999Kumaravel Selvakumar, Massimiliano Valentini +2 more
Angewandte Chemie International EditionPalladium-Catalyzed Allylic Alkylations without Isomerization—Dream or Reality?
84 Citations2000Uli Kazmaier, Franz L. Zumpe
Chemical CommunicationsSynthesis of amino acid derivatives via enantio- and diastereoselective Pd-catalyzed allylic substitutions with a non-stabilized enolate as nucleophileThis work is dedicated to Professor Walter Siebert on the occasion of his 65th birthday.
78 Citations2002Thomas D. Weiß, Günter Helmchen +1 more
A remarkable effect of the ligand on the diastereoselectivity of the substitution was found and enantiomeric excesses of up to 95% were achieved in Pd-catalyzed asymmetric alyllic substitutions with zinc enolates of glycine esters as nucleophiles.
Chemical CommunicationsEnantioselective allylic substitution catalyzed by an iridium complex: remarkable effects of the counter cation
75 Citations1999Kaoru Fuji, Naosumi Kinoshita +2 more
Chemistry - A European JournalPlatinum-Catalysed Allylic Alkylation: Reactivity, Enantioselectivity, and Regioselectivity
72 Citations2000A. John Blacker, Matthew L. Clarke +4 more
The use of platinum complexes as catalysts for allylic substitution has been studied and the development of a highly enantioselective reaction that makes use of chiral diphenylphosphinooxazoline ligands (abbreviated as (S)-PN) is also described.
The Journal of Organic ChemistryNew Chiral Phosphine−Phosphite Ligands in the Enantioselective Palladium-Catalyzed Allylic Alkylation
72 Citations2000Sirik Deerenberg, Henri Stephan Schrekker +5 more
Systematic variation of the ligand bridge and the phosphite moiety showed that the configuration of the product is controlled by the atropisomerism of the biphenyl substituent at the phosphine moiety.
Helvetica Chimica ActaHighly Enantio- and Regioselective Allylic Alkylations Catalyzed by Chiral [Bis(dihydrooxazole)]molybdenum Complexes
63 Citations2001Frank Glorius, Markus Neuburger +1 more
Angewandte ChemieNeue Liganden für die Steuerung der Regio- und Enantioselektivität von Pd-katalysierten allylischen Alkylierungen
59 Citations1998Roger Prétôt, Andreas Pfaltz
Angewandte ChemieChelatisierte Aminosäureesterenolate – effiziente Nucleophile für Palladium-katalysierte allylische Alkylierungen
55 Citations1999Uli Kazmaier, Franz L. Zumpe
European Journal of Organic ChemistryChelated Enolates of Amino Acid Esters − New and Efficient Nucleophiles for Isomerization-Free, Stereoselective Palladium-Catalyzed Allylic Substitutions
53 Citations2001Uli Kazmaier, Franz L. Zumpe
Angewandte ChemiePalladium-katalysierte Allylierungen ohne Isomerisierung – Wunsch oder Wirklichkeit?
47 Citations2000Uli Kazmaier, Franz L. Zumpe
Tetrahedron AsymmetryStructural control in palladium(II)-catalyzed enantioselective allylic alkylation by new chiral phosphine-phosphite and pyridine-phosphite ligands
40 Citations2000Carmela Grazia Arena, Dario Drommi +1 more
Tetrahedron Asymmetryα-Amino ester derivatives as nucleophiles in stereoselective palladium catalysed allylic substitution reactions
39 Citations1995I. Craig Baldwin, Jonathan M. J. Williams +1 more
Angewandte ChemieKatalytische asymmetrische Alkylierung von Nucleophilen ‐ asymmetrische Synthese α‐alkylierter Aminosäuren
37 Citations1997Barry M. Trost, Xavier Ariza
Chemical and Pharmaceutical BulletinAsymmetric Induction Reactions. VII. Palladium-Catalyzed Asymmetric .ALPHA.-Allylations of Carbonyl Compounds Using Chiral Sulfonamides as Chiral Ligands.
26 Citations1997Kunio Hiroi, Akira Hidaka +2 more
Angewandte ChemieDesigned Ligands as Probes for the Catalytic Binding Mode in Mo-Catalyzed Asymmetric Allylic Alkylation We thank the National Science Foundation and the National Institutes of Health for their generous support of the work carried out at Stanford. I.H. thanks the Japan Society for the Promotion of Science for a postdoctoral fellowship. Mass spectra were provided by the Mass Spectrometry Facility at the University of California, San Francisco, which is supported by the NIH Division of Research Resources.
18 Citations2002Barry M. Trost, Kalindi Dogra +8 more