Regioselective and enantioselective epoxidation catalyzed by metalloporphyrins.

Recent progress in regioselective and enantioselective epoxidations catalyzed by metalloporphyrins is discussed here, with an explanation of the biomimetic antecedents of this area and its relevance to synthetic applications. Classification of the catalysts that have been studied allows useful conclusions to be drawn about the development of this field. In particular, both the most promising biomimetic and practical catalysts have arisen from systems that can be systematically modified by convenient synthetic methodology.

[1]  J. I. Brauman,et al.  Enantioselective epoxidation of unfunctionalized olefins catalyzed by threitol-strapped manganese porphyrins , 1993 .

[2]  Cheal Kim,et al.  High-yield epoxidations with hydrogen peroxide and tert-butyl hydroperoxide catalyzed by iron(III) porphyrins: heterolytic cleavage of hydroperoxides , 1993 .

[3]  W. A. Nugent,et al.  Beyond Nature's Chiral Pool: Enantioselective Catalysis in Industry , 1993, Science.

[4]  F. Tani,et al.  Asymmetric Epoxidation of Simple Olefins by Chiral Bitetralin-Linked "Twin-Coronet" Porphyrin Catalysts. , 1993 .

[5]  Jianping Liu,et al.  Cation radical probes. Development and application to metalloporphyrin-catalyzed epoxidation , 1992 .

[6]  Earl V. Anderson.  Japanese firms emphasize technology management , 1992 .

[7]  B. Meunier.  Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage , 1992 .

[8]  E. Jacobsen,et al.  A Practical, Highly Enantioselective Synthesis of the Taxol Side Chain via Asymmetric Catalysis. , 1992 .

[9]  V. Schurig,et al.  Metal-Mediated Enantioselective Access to Unfunctionalized Aliphatic Oxiranes: Prochiral and Chiral Recognition , 1992 .

[10]  T. C. Bruice,et al.  Mechanism of alkene epoxidation by iron, chromium, and manganese higher valent oxo-metalloporphyrins , 1992 .

[11]  T. Aida,et al.  Asymmetric epoxidation of olefins catalyzed by manganese complexes of chiral "strapped" porphyrins with diastereotopic faces. A novel strategy for stereochemical modeling of the active site of cytochrome P-450 , 1992 .

[12]  E. Jacobsen,et al.  Enantioselective epoxidation of conjugated dienes and enynes. Trans-epoxides from cis-olefins , 1991 .

[13]  R. Paolesse,et al.  1H and 13C NMR characterization of a new chiral porphyrin, meso‐Tetra(α, β, α, β‐o‐camphanylamidophenyl)porphyrin, and its rhodium(III) complex , 1991 .

[14]  E. Jacobsen,et al.  Enantiomerically Pure Epoxychromans via Asymmetric Catalysis , 1991 .

[15]  F. Tani,et al.  Catalytic and asymmetric epoxidation of olefins with iron complexes of twin-coronet porphyrins. A mechanistic insight into the chiral induction of styrene derivatives , 1991 .

[16]  Wei Zhang,et al.  Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane , 1991 .

[17]  E. Jacobsen,et al.  Electronic tuning of asymmetric catalysts , 1991 .

[18]  R. L. Halterman,et al.  Catalytic asymmetric epoxidation of unfunctionalized alkenes using the first D4-symmetric metallotetraphenylporphyrin , 1991 .

[19]  Wei Zhang,et al.  Asymmetric olefin epoxidation with sodium hypochlorite catalyzed by easily prepared chiral manganese(III) salen complexes , 1991 .

[20]  T. Katsuki,et al.  Enantioselective epoxidation of unfunctionalized olefins using chiral (salen)manganese(III) complexes , 1991 .

[21]  K. A. Joergensen,et al.  Metallaoxetanes as intermediate in oxygen-transfer reactions - reality or fiction? , 1990 .

[22]  J. I. Brauman,et al.  Shape-selective olefin epoxidation catalyzed by manganese picnic basket porphyrins , 1990 .

[23]  Scott R. Wilson,et al.  Enantioselective Epoxidation of Unfunctionalized Olefins Catalyzed by (salen)Manganese Complexes , 1990 .

[24]  T. Katsuki,et al.  Catalytic asymmetric epoxidation of unfunctionalized olefins , 1990 .

[25]  J. Groves,et al.  Asymmetric hydroxylation, epoxidation, and sulfoxidation catalyzed by vaulted binaphthyl metalloporphyrins , 1990 .

[26]  T. J. Collins,et al.  A water-stable manganese(V)-oxo complex: definitive assignment of a .nu.Mnv.tplbond.O infrared vibration , 1990 .

[27]  T. Kodadek,et al.  Synthesis and characterization of the "chiral wall" porphyrin: a chemically robust ligand for metal-catalyzed asymmetric epoxidations , 1989 .

[28]  T. J. Collins,et al.  A manganese(V)-oxo complex , 1989 .

[29]  K. A. Joergensen.  Transition-metal-catalyzed epoxidations , 1989 .

[30]  T. Wagler,et al.  Optically active difunctionalized dioxocyclam macrocycles: ligands for nickel-catalyzed oxidation of alkenes , 1989 .

[31]  R. Neumann,et al.  Regioselective Oxidation Catalysis in Synthetic Phospholipid Vesicles. Membrane-Spanning Steroidal Metalloporphyrins , 1989 .

[32]  J. Groves,et al.  Synthesis, characterization, and reactivity of oxomanganese(IV) porphyrin complexes , 1988 .

[33]  J. I. Brauman,et al.  Synthesis, characterization, and x-ray structure of the ruthenium picnic-basket porphyrins , 1988 .

[34]  J. Dawson,et al.  Cytochrome P-450 and chloroperoxidase: thiolate-ligated heme enzymes. Spectroscopic determination of their active-site structures and mechanistic implications of thiolate ligation , 1987 .

[35]  K. Sharpless,et al.  Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization , 1987 .

[36]  R. Neumann,et al.  Membrane-spanning steroidal metalloporphyrins as site-selective catalysts in synthetic vesicles , 1987 .

[37]  K. Sharpless,et al.  Procedure for the catalytic asymmetric epoxidation of allylic alcohols in the presence of molecular sieves , 1986 .

[38]  J. Kochi,et al.  Epoxidation of olefins with cationic (salen)manganese(III) complexes. The modulation of catalytic activity by substituents. , 1986, Journal of the American Chemical Society.

[39]  J. Kochi,et al.  Mechanism of the chromium-catalyzed epoxidation of olefins. Role of oxochromium(V) cations , 1985 .

[40]  T. Kodadek,et al.  Epoxidation of olefins by cytochrome P-450 model compounds: kinetics and stereochemistry of oxygen atom transfer and origin of shape selectivity , 1985 .

[41]  I. Tabushi,et al.  Stereospecific, regioselective, and catalytic monoepoxidation of polyolefins by the use of a P-450 model, dihydrogen-dioxygen-TPP.cntdot.Mn-colloidal platinum , 1984 .

[42]  T. Kodadek,et al.  Epoxidation of olefins by cytochrome P-450 model compounds: mechanism of oxygen atom transfer. , 1984, Proceedings of the National Academy of Sciences of the United States of America.

[43]  J. Groves,et al.  Epoxidation reactions catalyzed by iron porphyrins. Oxygen transfer from iodosylbenzene , 1983 .

[44]  J. Groves,et al.  Catalytic asymmetric epoxidations with chiral iron porphyrins , 1983 .

[45]  T. P. Lockhart,et al.  2,3-Di-propyl-1,4-dehydrobenzene , 1980 .

[46]  W. C. Still.  (.+-.)-Periplanone-B. Total synthesis and structure of the sex excitant pheromone of the American cockroach , 1979 .

[47]  P. Rinaldi,et al.  Synthesis and enantiomeric purity determination of the optically active epoxide disparlure, sex pheromone of the gypsy moth , 1979 .

[48]  D. Jerina,et al.  Arene oxides: a new aspect of drug metabolism. , 1974, Science.