Binaphthyl‐Modified Quaternary Phosphonium Salts as Chiral Phase‐Transfer Catalysts: Asymmetric Amination of β‐Keto Esters
Angewandte ChemiePublished 31 October 2008Open access
Rongjun He, Xi‐Sheng Wang, Takuya Hashimoto, Keiji Maruoka
Citations154
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
Ein verlässlicher Phosphonium-PTC: Ein chirales Tetraalkylphosphoniumsalz wurde als Phasentransferkatalysator (PTC) für die asymmetrische Aminierung von β-Ketoestern in hoher Ausbeute und mit hohem ee-Wert eingesetzt (siehe Schema). Die asymmetrische Aminierung eines cyclischen fünfgliedrigen β-Ketoesters ist nützlich zur Herstellung eines Schlüsselintermediats bei der Synthese des Aldosereduktase-Inhibitors AS-3201 (Ranirestat).
Keywords
Chemistry
Chemical ReviewsEnantioselective Amino Acid Synthesis by Chiral Phase-Transfer Catalysis
827 Citations2003Keiji Maruoka, Takashi Ooi
Angewandte Chemie International EditionRecent Advances in Asymmetric Phase‐Transfer Catalysis
812 Citations2007Takashi Ooi, Keiji Maruoka
This work has shown that the use of chiral nonracemic onium salts and crown ethers as effective phase-transfer catalysts provides a reliable and general strategy for the practical asymmetric synthesis of highly valuable organic compounds.
Chemical ReviewsCatalytic Asymmetric Synthesis of α-Amino Acids
812 Citations2007Carmén Nájera, José M. Sansano
Journal of Synthetic Organic Chemistry JapanCatalytic Asymmetric Synthesis.
809 Citations1992Ryōji Noyori
Chemical ReviewsRecent Development and Application of Chiral Phase-Transfer Catalysts
797 Citations2007Takuya Hashimoto, Keiji Maruoka
Accounts of Chemical ResearchThe Enantioselective Synthesis of α-Amino Acids by Phase-Transfer Catalysis with Achiral Schiff Base Esters
758 Citations2004Martin O’Donnell
The development and application of chiral phase-transfer catalysis (PTC) for the enantioselective synthesis of optically active alpha-amino acid derivatives using achiral Schiff base esters developed in the author's laboratory and by others is reviewed.
Phase-Transfer Catalysis
706 Citations1994Charles M. Starks, Charles L. Liotta +1 more
Modern Amination Methods
548 Citations2000
Accounts of Chemical ResearchAsymmetric Phase-Transfer Catalysis Utilizing Chiral Quaternary Ammonium Salts: Asymmetric Alkylation of Glycine Imines
548 Citations2004Barry Lygo, Benjamin I. Andrews
O-Alkyl N-anthracenylmethyl derivatives of Cinchona alkaloids can function as enantioselective phase-transfer catalysts, resulting in the development of a new highly selective catalyst and opening up the potential of further expanding the range of alpha-amino acid derivatives that can be prepared.
Angewandte Chemie International EditionRecent Advances in Catalytic, Enantioselective α Aminations and α Oxygenations of Carbonyl Compounds
354 Citations2005Jacob M. Janey
A synopsis of this ever-growing field of catalytic, enantioselective Lewis acid and Lewis base catalysis is provided and some of the challenges that still remain are highlighted.
Medical Entomology and ZoologyPhase-Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives
325 Citations1994Charles M. Starks, Charles L. Liotta +1 more
Journal of the American Chemical SocietyAsymmetric Construction of Quaternary Stereocenters by Direct Organocatalytic Amination of α-Substituted α-Cyanoacetates and β-Dicarbonyl Compounds
281 Citations2004Steen Saaby, Marco Bella +1 more
The first organocatalytic highly enantioselective reactions of substituted alpha-cyanoacetates and beta-dicarbonyl compounds with azodicarboxylates are reported, and a two-step procedure for the cleavage of the hydrazine N-N bond using SmI2 is demonstrated.
Journal of the American Chemical SocietyAxially Chiral Guanidine as Highly Active and Enantioselective Catalyst for Electrophilic Amination of Unsymmetrically Substituted 1,3-Dicarbonyl Compounds
231 Citations2006Masahiro Terada, Megumi Nakano +1 more
A newly designed axially chiral guanidine is found to function as an effective platform for asymmetric induction at the alpha-carbon of unsymmetrically substituted 1,3-dicarbonyl compounds.
Angewandte Chemie International EditionAsymmetric Phase-Transfer Catalysis
214 Citations1999Adam Nelson
Both in the laboratory and industrially, phase-transfer catalysis offers the potential to induce asymmetry into reactions with anionic intermediates.
Journal of the American Chemical SocietyCatalytic Asymmetric Direct α-Amination Reactions of 2-Keto Esters: A Simple Synthetic Approach to Optically Active <i>syn</i>-β-Amino-α-hydroxy Esters
209 Citations2002Karsten Juhl, Karl Anker Jørgensen
Angewandte ChemieFortschritte bei asymmetrischen Phasentransferkatalysen
203 Citations2007Takashi Ooi, Keiji Maruoka
Angewandte Chemie International EditionCatalytic, Highly Enantioselective, Direct Amination of β‐Ketoesters
196 Citations2003Mauro Marigo, Karsten Juhl +1 more
Organic LettersHighly Enantioselective Amination of α-Substituted α-Cyanoacetates with Chiral Catalysts Accessible from Both Quinine and Quinidine
187 Citations2004Xiaofeng Liu, Hongming Li +1 more
The use of 6‘-OH-modified cinchona alkaloids that are accessible from either quinine or quinidine for the development of a highly enantioselective amination of α,α-disubstituted carbonyl compounds that is suitable for the creation of nitrogen-substituting quaternary stereocenters in either the R or S configuration is described.
European Journal of Organic ChemistryAsymmetric Electrophilic α‐Amination of Carbonyl Groups
173 Citations2004Christine Greck, Bruno Drouillat +1 more
Journal of Medicinal ChemistryNovel, Highly Potent Aldose Reductase Inhibitors: (<i>R</i>)-(−)-2-(4-Bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo[1,2-<i>a</i>]pyrazine- 4-spiro-3‘-pyrrolidine-1,2‘,3,5‘-tetrone (AS-3201) and Its Congeners
123 Citations1998Toshiyuki Negoro, Makoto Murata +7 more
The preparation and structure-activity relationship (SAR) of tetrahydropyrrolopyrazine derivatives including a novel ARI, AS-3201, is reported, which was selected as the candidate for clinical development.
Journal of the American Chemical SocietyEn Route to an Efficient Catalytic Asymmetric Synthesis of AS-3201
120 Citations2007Tomoyuki Mashiko, Keiichi Hara +4 more
The amination reaction proceeded efficiently with as little as 1 mol % of catalyst loading, allowing for an efficient access to the key intermediate for the synthesis of AS-3201, a potent aldose reductase inhibitor.
Tetrahedron LettersAsymmetric phase-transfer alkylation catalyzed by a chiral quaternary phosphonium salt with a multiple hydrogen-bonding site
106 Citations1998Kei Manabe
Angewandte ChemieFortschritte bei katalytischen enantioselektiven α‐Aminierungen und α‐Oxygenierungen von Carbonylverbindungen
105 Citations2005Jacob M. Janey
The Journal of Organic ChemistryHighly Enantioselective Electrophilic Amination and Michael Addition of Cyclic β-Ketoesters Induced by Lanthanides and (<i>S</i>,<i>S</i>)-ip-pybox: The Mechanism
95 Citations2007Josep M. Comelles, Àlex Pericas +8 more
Intermediates based on simultaneous coordination of the lanthanide to both (S,S)-ip-box and beta-ketoester (in keto and enolate forms) are detected by means of ESI mass spectrometry and NMR experiments, and a possible mechanism is proposed through theoretical calculations.
Organic LettersCu- and Pd-Catalyzed Asymmetric One-Pot Tandem Addition−Cyclization Reaction of 2-(2‘,3‘-Alkadienyl)-β-keto Esters, Organic Halides, and Dibenzyl Azodicarboxylate: An Effective Protocol for the Enantioselective Synthesis of Pyrazolidine Derivatives
95 Citations2004Shengming Ma, Ning Jiao +6 more
Optically active pyrazolidine derivatives have been constructed by the Cu- and Pd-catalyzed asymmetric one-pot tandem addition-cyclization reaction of 2-(2',3'-dienyl)-beta-ketoesters, organic halides, and dibenzyl azodicarboxylate.
CHIMIA International Journal for ChemistryRecent Developments in Enantioselective Phase Transfer Catalysis Using Chiral Ammonium Salts
92 Citations2006Jérôme Vachon, Jérôme Lacour
SynlettEnantioselective Organocatalytic Diels Aminations: α-Aminations of Cyclic β-Keto Esters and β-Keto Lactones with Cinchonidine and Cinchonine
89 Citations2004Petri M. Pihko, Antti Pohjakallio
Tetrahedron LettersCatalytic enantioselective electrophilic α-amination of β-ketoesters catalyzed by chiral palladium complexes
89 Citations2006Young Ku Kang, Dae Young Kim
Chemical CommunicationsExploiting C3-symmetry in the dynamic coordination of a chiral trisoxazoline to copper(ii): improved enantioselectivity, and catalyst stability in asymmetric lewis acid catalysis
88 Citations2005C. Foltz, Björn Stecker +4 more
Chiral C3-symmetric trisoxazolines are highly efficient stereodirecting ligands in enantioselective Cu(II) Lewis acid catalysis which is based on the concept of a stereoelectronic hemilability of the divalent copper.
Diabetes CareAldose Reductase Inhibition by AS-3201 in Sural Nerve From Patients With Diabetic Sensorimotor Polyneuropathy
88 Citations2004Vera Bril, R. A. Buchanan +1 more
Whether AS-3201 penetrates the sural nerve and inhibits sorbitol and fructose accumulation in patients with diabetic sensorimotor polyneuropathy (DSP) is investigated to confirm the electrophysiological suggestion that the drug delays progression or leads to regression of DSP.
Organic LettersAn Improved Lanthanum Catalyst System for Asymmetric Amination: Toward a Practical Asymmetric Synthesis of AS-3201 (Ranirestat)
65 Citations2008Tomoyuki Mashiko, Naoya Kumagai +1 more
A catalytic asymmetric amination with a lanthanum/amide complex was significantly improved and a practical synthesis of a key intermediate for AS-3201, a highly potent aldose reductase inhibitor was performed.
Angewandte ChemieCatalytic, Highly Enantioselective, Direct Amination of β‐Ketoesters
62 Citations2003Mauro Marigo, Karsten Juhl +1 more
Tetrahedron AsymmetryConsecutive catalytic electrophilic fluorination/amination of β-keto esters: toward α-fluoro-α-amino acids?
61 Citations2006Dominique Huber, Kyrill Stanek +1 more
Asymmetric Phase Transfer Catalysis
60 Citations2000Takayuki Shioiri, Shigeru Arai
Chiral phase transfer catalysis
51 Citations1997Takayuki Shioiri
BiochemistryStereospecific Interaction of a Novel Spirosuccinimide Type Aldose Reductase Inhibitor, AS-3201, with Aldose Reductase
46 Citations2001Masuo Kurono, Iwao Fujiwara +1 more
Results suggested that the selective binding to the E-NADP(+) complex arises from the predominance of this enzyme form during steady-state turnover rather than from binding specificity.
Biochemical PharmacologyStereospecific recognition of a spirosuccinimide type aldose reductase inhibitor (AS-3201) by plasma proteins: A significant role of specific binding by serum albumin in the improved potency and stability
41 Citations2005Masuo Kurono, Akihito Fujii +3 more
The present results, together with preliminary absorption and distribution profiles, provide valuable information on the stereospecific pharmacokinetic and pharmacodynamic properties of the R-isomer relevant for the therapeutic treatment of diabetic complications.
NIPPON KAGAKU KAISHIStructural Transformation of Tetrabutylphosphonium Bromide Phase Transfer Catalyst in Chloride-Fluoride Exchange Reaction.
8 Citations1991Shigeaki Yonemori, Yasuo Hayashi +2 more
RWTH Publications (RWTH Aachen)Neue optisch aktive Phosphoniumsalze als Phasentransferkatalysatoren sowie die Verwendung der korrespondierenden Phosphane in der asymmetrischen Katalyse
3 Citations2003Manuela Köhler