Investigation of site selectivity of the stereoselective deprotonation of cyclohexene oxide using kinetic resolution of isotopic enantiomers in natural abundance

[1]  P. Ahlberg,et al.  Composition and structure of activated complexes in stereoselective deprotonation of cyclohexene oxide by a mixed dimer of chiral lithium amide and lithiated imidazole , 2004 .

[2]  D. B. Collum,et al.  Lithium 2,2,6,6-Tetramethylpiperidide-Mediated α- and β-Lithiations of Epoxides: Solvent-Dependent Mechanisms , 2003 .

[3]  P. Ahlberg,et al.  Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline , 2002 .

[4]  P. Ahlberg,et al.  Improved enantioselectivity by using novel bulk bases in chiral lithium amide catalysed deprotonations: mixed dimers as reagents and catalysts , 2002 .

[5]  A. Seki,et al.  Catalytic enantioselective rearrangement of meso-epoxides mediated by chiral lithium amides in the presence of excess cross-linked polymer-bound lithium amides , 2002 .

[6]  Kevin P. Gable,et al.  Kinetic isotope effects in cycloreversion of rhenium (V) diolates. , 2002, Journal of the American Chemical Society.

[7]  P. Andersson,et al.  New catalysts for the base-promoted isomerization of epoxides to allylic alcohols. Broadened scope and near-perfect asymmetric induction. , 2002, The Journal of organic chemistry.

[8]  P. Ahlberg,et al.  2-(Lithiomethyl)-1-methylimidazole as a non-reactive bulk base and its novel mixed dimer with a chiral lithium amide in catalytic stereoselective deprotonation , 2001 .

[9]  P. Ahlberg,et al.  A novel mixed dimer of a norephedrine-derived chiral lithium amide and 2-lithium-1-methylimidazole, and catalytic enantioselective deprotonation of cyclohexene oxide. , 2001, Chemistry.

[10]  Ben-Li Zhang,et al.  A simple method for the precise and simultaneous determination of primary and multiple secondary kinetic deuterium isotope effects in organic reactions at natural abundance , 2001 .

[11]  P. Ahlberg,et al.  Kinetic and computational studies of the composition and structure of activated complexes in the asymmetric deprotonation of cyclohexene oxide by a norephedrine-derived chiral lithium amide , 2001 .

[12]  P. Andersson,et al.  Allylic Alcohols via Catalytic Asymmetric Epoxide Rearrangement , 2000 .

[13]  C. Hang,et al.  13C and (2)H kinetic isotope effects and the mechanism of Lewis acid-catalyzed ene reactions of formaldehyde. , 2000, The Journal of organic chemistry.

[14]  C. Hang,et al.  Isotope effects and the experimental transition state for a prototypical thermal ene reaction , 1999 .

[15]  P. O’Brien,et al.  A new norephedrine-derived chiral base for epoxide rearrangement reactions , 1999 .

[16]  D. B. Collum,et al.  Hemi-Labile Ligands in Organolithium Chemistry: Rate Studies of the LDA-Mediated α- and β-Metalations of Epoxides , 1999 .

[17]  M. P. Meyer,et al.  Reinvestigation of the Isotope Effects for the Claisen and Aromatic Claisen Rearrangements: The Nature of the Claisen Transition States , 1999 .

[18]  P. Ahlberg,et al.  Composition of the activated complex in the stereoselective deprotonation of cyclohexene oxide by a chiral lithium amide , 1999 .

[19]  M. Szymanski,et al.  Simultaneous Determination of Intermolecular and Intramolecular 13C and 2H Kinetic Isotope Effects at Natural Abundance , 1999 .

[20]  S. R. Merrigan,et al.  13C and 2H kinetic isotope effects and the mechanism of bromination of 1-pentene under synthetic conditions. , 1999, Organic letters.

[21]  D. Barton,et al.  Separation of the primary and secondary kinetic isotope effects at a reactive center using starting material reactivities. Application to the FeCl3-Catalyzed oxidation of CH bonds with tert-butyl hydroperoxide , 1999 .

[22]  P. Arvidsson,et al.  Computational study of solvation and stereoselectivity in deprotonation of cyclohexene oxide by a chiral lithium amide , 1999 .

[23]  M. Drew,et al.  Mechanism and applications of lithium amide-induced asymmetric rearrangements of 4-substituted and 4,4-disubstituted cyclopentene oxides to cyclopentenols , 1999 .

[24]  E. Noe,et al.  Conformational Study of Cyclohexene Oxide by Dynamic NMR Spectroscopy and Ab Initio Molecular Orbital Calculations , 1998 .

[25]  K. Houk,et al.  Experimental and Theoretical Kinetic Isotope Effects for Asymmetric Dihydroxylation. Evidence Supporting a Rate-Limiting “(3 + 2)” Cycloaddition , 1997 .

[26]  V. Singh,et al.  Design, Synthesis, and Application of Chiral Nonracemic Lithium Amide Bases in Enantioselective Deprotonation of Epoxides. , 1996, The Journal of organic chemistry.

[27]  J. Gajewski,et al.  Mechanisms of the Base-Induced Isomerizations of Cyclopentene and Cyclohexene Oxides: Influence of Structure and Solvent on α and β Proton Removal , 1996 .

[28]  A. Thomas,et al.  High-Precision Simultaneous Determination of Multiple Small Kinetic Isotope Effects at Natural Abundance , 1995 .

[29]  S. Inoue,et al.  Catalytic enantioselective deprotonation of meso-epoxides by the use of chiral lithium amide , 1994 .

[30]  Maryvonne L. Martin,et al.  Simultaneous determination of primary and secondary thermodynamic isotope effects in tautomeric equilibria , 1993 .

[31]  Ben-Li Zhang.  Application of natural abundance 2H NMR. Simultaneous measurement of primary and secondary kinetic deuterium isotope effects , 1988 .

[32]  R. Pascal,et al.  Measurement of deuterium kinetic isotope effects in organic and biochemical reactions by natural abundance deuterium NMR spectroscopy , 1986 .

[33]  R. Pascal,et al.  Measurement of deuterium kinetic isotope effects in organic reactions by natural-abundance deuterium NMR spectroscopy , 1984 .

[34]  G. Martin,et al.  Deuterium labelling at the natural abundance level as studied by high field quantitative 2H NMR , 1981 .

[35]  J. Whitesell,et al.  Asymmetric induction. 3. Enantioselective deprotonation by chiral lithium amide bases , 1980 .

[36]  J. Crandall,et al.  Base-promoted reactions of epoxides. VI. Bicyclo[2.2.1]heptene and bicyclo[2.2.2]octene oxides , 1971 .

[37]  R. Thummel,et al.  Stereochemistry of the base-induced rearrangement of epoxides to allylic alcohols , 1970 .

[38]  R. Thummel,et al.  Stereoselectivity of the base-induced conversion of epoxides to allylic alcohols , 1969 .

[39]  J. Crandall,et al.  Base-promoted reactions of epoxides. V. 1-Alkylcycloalkene oxides , 1968 .

[40]  G. A. Berchtold,et al.  Proximity Effects. XXII. Evidence for the Mechanism of the Reaction of Mediumsized Ring Epoxides with Lithium Diethylamide , 1960 .

[41]  E. Trumbull,et al.  Base-catalyzed Rearrangement of Epoxides , 1958 .