Ketone-directed peracid epoxidation of cyclic alkenes

Ketone carbonyl groups are shown to direct the peracid epoxidation of cyclic alkenes with greater selectivity than that displayed by esters. An 18O labelling study is used to show that a dioxirane intermediate is not involved in these reactions.

[1]  U. Hacksell,et al.  Stereoselective Epoxidation of Allylic Carbamates with m-Chloroperbenzoic Acid: The Role of Cooperative Coordination , 1995 .

[2]  A. Armstrong,et al.  Ketone-directed peracid epoxidation , 1994 .

[3]  U. Hacksell,et al.  Stereoselective Epoxidation of Phe-Gly and Phe-Phe Vinyl Isosteres , 1994 .

[4]  R. Persky,et al.  Improved stereocontrolled synthesis of threo peptidyl epoxides , 1994 .

[5]  T. Olsson,et al.  Iodotrimethylsilane-promoted additions of monoorganocopper compounds to .alpha.,.beta.-unsaturated ketones, esters, and lactones , 1993 .

[6]  Davidr . Evans,et al.  Substrate-directable chemical reactions , 1993 .

[7]  Graham B Jones,et al.  The Claisen rearrangement in synthesis: Acceleration of the Johnson orthoester protocol en route to bicyclic lactones , 1993 .

[8]  T. J. Simpson,et al.  Biosynthetic studies on tajixanthone and shamixanthone, polyketide hemiterpenoid metabolites of Aspergillus variecolor , 1992 .

[9]  J. Bialas,et al.  Kurzmitteilung / Short Communication A Convenient Preparation of Acetone Solutions of Dimethyldioxirane , 1991 .

[10]  C. Fotsch,et al.  Stereochemical control in reactions of nucleophiles with oxocarbenium ions formed by intramolecular opening of activated epoxides by neighboring carbonyl groups , 1991 .

[11]  P. Kočovský,et al.  Steric control of epoxidation by carbamate and amide groups. Evidence for the carbonyl-directed epoxidation , 1990 .

[12]  R. W. Hoffmann,et al.  Allylic 1,3-strain as a controlling factor in stereoselective transformations , 1989 .

[13]  R. Halcomb,et al.  On the direct epoxidation of glycals: application of a reiterative strategy for the synthesis of .beta.-linked oligosaccharides , 1989 .

[14]  F. Mohamadi,et al.  Carbonyl directed epoxidation in γ,δ-unsaturated acid derivatives , 1989 .

[15]  P. Kočovský Steric control of epoxidation by allylic and homoallylic carbamate groups , 1988 .

[16]  F. Tureček,et al.  A contribution to peroxy acid oxidation of α,β-unsaturated ketones and linearly conjugated dienones: reactions in the cholestane series , 1988 .

[17]  Carl R. Johnson,et al.  Trimethylsilyl chloride/tetramethylethylenediamine facilitated additions of organocopper reagents (RCu) to enones , 1987 .

[18]  Sung Soo Kim,et al.  Direct conversion of carboxylic acids and carboxylic esters into S,S′-diphenyl acetals and phenyl sulfides with thexylphenylthioborane , 1987 .

[19]  T. Mano,et al.  Inter- and intramolecular epoxidation utilizing silyl-protected peroxy ester and copper salt , 1987 .

[20]  S. Hsu,et al.  Ester-directed alkene functionalization. A potential approach to trichothecene synthesis , 1986 .

[21]  H. Wasserman,et al.  Application of the carbonyl epoxide rearrangement to the formation of dioxabicycloalkanes and alkenes. Synthesis of the mus musculus pheromone. , 1986 .

[22]  V. Ramachandran,et al.  OXIDATION OF ACETONE UNDER BAEYER‐VILLIGER CONDITIONS: EVIDENCE FOR FORMATION OF ACETONE CARBONYL OXIDE OR ITS ISOMERIC DIOXIRANE , 1979 .

[23]  R. Murray,et al.  Epoxidation of olefins with carbonyl oxides , 1979 .

[24]  J. Risley,et al.  /sup 18/O isotope shift upon /sup 13/C NMR spectra and its application to the study of oxygen exchange kinetics , 1979 .

[25]  T. Brocksom,et al.  Simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene , 1970 .

[26]  J. Edwards,et al.  Synthetic studies on insect hormones. VII. An approach to stereospecific synthesis of juvenile hormones , 1968 .

[27]  H. Gilman,et al.  Secondary and Tertiary Alkyllithium Compounds and Some Interconversion Reactions with Them1 , 1941 .