Asymmetric Baeyer-Villiger Reaction with Hydrogen Peroxide Catalyzed by a Novel Planar-Chiral Bisflavin
Angewandte ChemiePublished 3 July 2002
Shun‐Ichi Murahashi, Satoshi Ono, Yasushi Imada
Citations65
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
Der chirale Organokatalysator Bisflavin 1 katalysiert asymmetrische Baeyer-Villiger-Reaktionen von Cyclobutanonen mit H2O2 (siehe Schema). Die entsprechenden Lactone werden mit bis zu 74 % ee erhalten.
Keywords
ChemistryMaterials Science
Journal of the American Chemical SocietyDevelopment and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model
13,063 Citations1985Michael J. S. Dewar, Eve G. Zoebisch +2 more
Journal of the American Chemical SocietyThe nature of .pi.-.pi. interactions
5,268 Citations1990Christopher A. Hunter, Jeremy K. M. Sanders
European Journal of Organic Chemistry100 Years of Baeyer–Villiger Oxidations
568 Citations1999Michael Renz, Bernard Meunier
Angewandte Chemie International Edition in EnglishSynthetic Aspects of Metal‐Catalyzed Oxidations of Amines and Related Reactions
533 Citations1995Shun‐Ichi Murahashi
Three general approaches provide highly useful strategies for synthesis of fine chemicals and biologically active compounds such as alkaloids, amino acids, and β-lactams: biomimetic, catalytic oxidations of amines and related compounds, and lowvalent ruthenium complexes and peroxides.
Angewandte Chemie International Edition in EnglishEnzymic Baeyer–Villiger Oxidations by Flavin‐Dependent Monooxygenases
259 Citations1988Christopher T. Walsh, Y.‐C. Jack Chen
Bacteria, capable of growth on aliphatic molecules, that contain enzymes which can catalyze Baeyer-Villiger reactions, raise the possibility that these biocatalysts can be useful as reagents in organic synthesis.
Angewandte Chemie International Edition in EnglishOptically Active Lactones from a Baeyer–Villiger‐Type Metal‐Catalyzed Oxidation with Molecular Oxygen
231 Citations1994Carsten Bolm, Gunther Schlingloff +1 more
Organic LettersElectrophilic Activation of Hydrogen Peroxide: Selective Oxidation Reactions in Perfluorinated Alcohol Solvents
170 Citations2000Karine Neimann, Ronny Neumann
Use of perfluorinated alcoholic solvents in the absence of catalysts allowed electrophilic activation of hydrogen peroxide toward epoxidation of alkenes and the Baeyer-Villiger oxidation of ketones.
OrganometallicsPlatinum-Catalyzed Oxidations with Hydrogen Peroxide: Enantiospecific Baeyer-Villiger Oxidation of Cyclic Ketones
161 Citations1994Andrea Gusso, Carla Baccin +2 more
The Journal of Organic ChemistryMicrobiological transformations. 22. Microbiologically mediated Baeyer-Villiger reactions: a unique route to several bicyclic .gamma.-lactones in high enantiomeric purity
146 Citations1992Véronique Alphand, Roland Furstoss
Journal of the American Chemical SocietyFlavin-catalyzed oxidation of amines and sulfur compounds with hydrogen peroxide
142 Citations1989Shun‐Ichi Murahashi, Tetsuya Oda +1 more
Angewandte ChemieSynthetische Aspekte metallkatalysierter Oxidationen von Aminen und verwandte Reaktionen
108 Citations1995Shun‐Ichi Murahashi
The Journal of Organic ChemistryFlavin-Catalyzed Baeyer−Villiger Reaction of Ketones: Oxidation of Cyclobutanones to γ Lactones Using Hydrogen Peroxide
95 Citations1996Claudio Mazzini, Jacques Lebreton +1 more
Justus Liebig s Annalen der ChemieStudien in der Flavin‐Reihe, XVIII. Die reduktive Alkylierung des Flavinkerns<sup>2)</sup>; Struktur und Reaktivität von Dihydroflavinen
93 Citations1973Sandro Ghisla, Ursula Hartmann +2 more
Tetrahedron LettersCationic Co(III)(salen)-catalyzed enantioselective Baeyer–Villiger oxidation of 3-arylcyclobutanones using hydrogen peroxide as a terminal oxidant
92 Citations2001Tatsuya Uchida, Tsutomu Katsuki
Tetrahedron LettersAsymmetric Baeyer-Villiger oxidation of cyclobutanones
82 Citations1996Margus Lopp, Anne Paju +2 more
Angewandte ChemieOptisch aktive Lactone durch metallkatalysierte Baeyer‐Villiger‐analoge Oxidation mit molekularem Sauerstoff
81 Citations1994Carsten Bolm, Gunther Schlingloff +1 more
Angewandte ChemieEnzymatische Baeyer‐Villiger‐Oxidationen durch flavinabhängige Monooxygenasen
80 Citations1988Christopher T. Walsh, Y.‐C. Jack Chen
SynlettEnantioselective Metal-catalyzed Baeyer-Villiger Oxidation of Cyclobutanones
78 Citations1997Carsten Bolm, T. Khanh Luong +1 more
Journal of the Chemical Society Chemical CommunicationsEnantioselective oxidation of sulphides with chiral 4a-hydroperoxyflavin
61 Citations1988Seiji Shinkai, Toshiro Yamaguchi +2 more
Canadian Journal of ChemistryChiral aluminum complexes as catalysts in asymmetric Baeyer-Villiger reactions of cyclobutanones
59 Citations2001Carsten Bolm, Oliver Beckmann +1 more
SynlettFluorinated Alcohols: Effective Solvents for Uncatalysed Epoxidations with Aqueous Hydrogen Peroxide
58 Citations2001Michiel C. A. van Vliet, Isabel W. C. E. Arends +1 more
Helvetica Chimica ActaStudien in der Lumiflavin‐Reihe VI. Alkylierungs‐ und Desalkylierungs‐Reaktionen an (Iso)alloxazinen; 1,3,10‐Trimethylflavosemichinone
57 Citations1960Peter Hemmerich, B. Prijs +1 more
It is shown, that flavin catabolism (N-10-dealkylation) occurs in the semiquinonoid state at room temperature, and is neither confined to hydroxyalkylflavins, nor to specific catalysis by light.
SynlettEnantioselective Baeyer-Villiger Oxidations Catalyzed by Chiral Magnesium Complexes
55 Citations2001Carsten Bolm, Oliver Beckmann +2 more
Angewandte Chemie International Edition in EnglishPreparative Scale Directed Resolution of Enantiomeric Amines <i>via</i> Liquid Chromatography of Diastereomeric 4‐Hydroxybutyramides
31 Citations1979Günter Helmchen, Günter Nill
Angewandte ChemieGezielte präparative Trennung enantiomerer Amine via Flüssigkeitschromatographie diastereomerer 4‐Hydroxybutyramide
28 Citations1979Günter Helmchen, Günter Nill
Chemische Berichte[3.3]Isoalloxazinophanes and Arene‐Bridged Bis(isoalloxazines): Syntheses, Characterizations and Properties Related to Intramolecular Interactions
12 Citations1994Heinz A. Staab, Peer Kirsch +3 more
Tetrahedron AsymmetrySynthesis and reactivities of a novel flavoenzyme model, 5-deazaflavin with C2-symmetry
3 Citations1997Reiko Yanada, Yoshiyuki Yoneda +5 more