Log in

Relevant bibliographies by topics / Oxaziridine chemistry

Contents

Journal articles
Dissertations / Theses
Book chapters

Academic literature on the topic 'Oxaziridine chemistry'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

Create a spot-on reference in APA, MLA, Chicago, Harvard, and other styles

Select a source type:

Consult the lists of relevant articles, books, theses, conference reports, and other scholarly sources on the topic 'Oxaziridine chemistry.'

Next to every source in the list of references, there is an 'Add to bibliography' button. Press on it, and we will generate automatically the bibliographic reference to the chosen work in the citation style you need: APA, MLA, Harvard, Chicago, Vancouver, etc.

You can also download the full text of the academic publication as pdf and read online its abstract whenever available in the metadata.

Journal articles on the topic "Oxaziridine chemistry"

1

Meladinis, Vassilios, Uwe Verfürth, and Rudolf Herrmann. "Highly Efficient Camphor-Derived Oxaziridines for the Asymmetric Oxidation of Sulfides to Chiral Sulfoxides." Zeitschrift für Naturforschung B 45, no. 12 (December 1, 1990): 1689–94. http://dx.doi.org/10.1515/znb-1990-1216.

Full text

Abstract:

Chiral N-sulfonyl-oxaziridines derived from 8-camphorsulfonic acid and fenchone have been evaluated as asymmetric oxidizing agents for the conversion of sulfides to chiral sulfoxides. There is no correlation between the redox potentials nor the 17O NMR chemical shifts of the oxaziridines and their relative oxidation rates, nor with the enantiomeric excesses achieved, indicating that steric effects are responsible for their behaviour. The results are consistent with an attack of one sulfur lone pair at the oxaziridine oxygen in such a way that both sulfur lone pairs lie in the plane of the oxaziridine ring. The most efficient oxaziridines, the camphorlactone-sulfonyloxaziridine [(4aS,9 aR)-10,10-dimethyl-6,7-dihydro-4 H-4 a,7-methano-oxazirino[3,2-j]oxepino[3,4-c]isothiazol-9(5H)-one 3,3-dioxide] and the 3-endo-bromocamphorsulfonyloxaziridine [(4aS,8 S,8 aR)-8-bromo-9,9-dimethyl-5,6,7,8-tetrahydro-4 H- 4a,7-methano-oxazirino-2,1-benzisothiazole 3,3-dioxide] allow the preparation of chiral sulfoxides with up to 85% enantiomeric excess.

APA, Harvard, Vancouver, ISO, and other styles

2

Davis, Franklin A., James C. Towson, Michael C. Weismiller, Sankar Lal, and Patrick J. Carroll. "Chemistry of oxaziridines. 11. (Camphorylsulfonyl)oxaziridine: synthesis and properties." Journal of the American Chemical Society 110, no. 25 (December 1988): 8477–82. http://dx.doi.org/10.1021/ja00233a025.

Full text

APA, Harvard, Vancouver, ISO, and other styles

3

Wagner, Gabriele, Uwe Verfürth, and Rudolf Herrmann. "Chemistry of Fenchonesulfonic Acid Derivatives." Zeitschrift für Naturforschung B 50, no. 2 (February 1, 1995): 283–88. http://dx.doi.org/10.1515/znb-1995-0223.

Full text

Abstract:

(1 S) - (+)-Fenchone is sulfonated by SO3 or H2SO4/acetic anhydride in the bridgehead methyl group. This could be confirmed by NMR techniques (INADEQUATE). The fenchonesulfonic acid obtained is converted (SOCl2/NH3) to the cyclic fenchonesulfonimide, which can be oxidized to the corresponding oxaziridine, in close analogy to 10-camphorsulfonimide. Improved procedures for this reaction sequences are given. During the treatment of the sulfonic acid with thionyl chloride, a byproduct with a rearranged bicyclic skeleton is observed whose structure has been determined by ozonolytic degradation and NMR techniques. A possible mechanism for this rearrangement is suggested, based on MNDO calculations of the intermediate carbocations. The fenchonesulfonyloxaziridine oxidizes sulfides to chiral sulfoxides with appreciable enantiomeric excess, but very low reaction rate. A comparison with camphor-derived oxaziridines having similar steric requirements is made.

APA, Harvard, Vancouver, ISO, and other styles

4

Elledge, Susanna K., Hai L. Tran, Alec H. Christian, Veronica Steri, Byron Hann, F. Dean Toste, Christopher J. Chang, and James A. Wells. "Systematic identification of engineered methionines and oxaziridines for efficient, stable, and site-specific antibody bioconjugation." Proceedings of the National Academy of Sciences 117, no. 11 (March 2, 2020): 5733–40. http://dx.doi.org/10.1073/pnas.1920561117.

Full text

Abstract:

The field of chemical modification of proteins has been dominated by random modification of lysines or more site-specific labeling of cysteines, each with attendant challenges. Recently, we have developed oxaziridine chemistry for highly selective modification of methionine called redox-activated chemical tagging (ReACT) but have not broadly tested the molecular parameters for efficient and stable protein modification. Here we systematically scanned methionines throughout one of the most popular antibody scaffolds, trastuzumab, used for antibody engineering and drug conjugation. We tested the expression, reactivities, and stabilities of 123 single engineered methionines distributed over the surface of the antibody when reacted with oxaziridine. We found uniformly high expression for these mutants and excellent reaction efficiencies with a panel of oxaziridines. Remarkably, the stability to hydrolysis of the sulfimide varied more than 10-fold depending on temperature and the site of the engineered methionine. Interestingly, the most stable and reactive sites were those that were partially buried, presumably because of their reduced access to water. There was also a 10-fold variation in stability depending on the nature of the oxaziridine, which was determined to be inversely correlated with the electrophilic nature of the sulfimide. Importantly, the stabilities of the best analogs were sufficient to support their use as antibody drug conjugates and potent in a breast cancer mouse xenograft model over a month. These studies provide key parameters for broad application of ReACT for efficient, stable, and site-specific antibody and protein bioconjugation to native or engineered methionines.

APA, Harvard, Vancouver, ISO, and other styles

5

Davis, Franklin A., Aurelia C. Sheppard, Bang Chi Chen, and M. Serajul Haque. "Chemistry of oxaziridines. 14. Asymmetric oxidation of ketone enolates using enantiomerically pure (camphorylsulfonyl)oxaziridine." Journal of the American Chemical Society 112, no. 18 (August 1990): 6679–90. http://dx.doi.org/10.1021/ja00174a035.

Full text

APA, Harvard, Vancouver, ISO, and other styles

6

Meladinis, Vassilios, Rudolf Herrmann, Oliver Steigelmann, and Gerhard Müller. "Synthesis and Structure of a New Chiral Oxaziridine from (3-Oxo-camphorsulfonyl)imine." Zeitschrift für Naturforschung B 44, no. 11 (November 1, 1989): 1453–58. http://dx.doi.org/10.1515/znb-1989-1122.

Full text

Abstract:

Oxidation of (3-oxo-camphorsulfonyl)imine (1) by magnesium monoperoxyphthalate does not lead to the oxaziridine obtained with 3-chloro-perbenzoic acid, but to a new chiral oxaziridine containing an additional oxygen atom (Baeyer-Villiger type oxidation). The structure of the product is established by X-ray crystallography, and reaction pathways for the oxidation of 1 by peracids are discussed.

APA, Harvard, Vancouver, ISO, and other styles

7

Armstrong, Alan, Ian D. Edmonds, Martin E. Swarbrick, and Nigel R. Treweeke. "Electrophilic amination of enolates with oxaziridines: effects of oxaziridine structure and reaction conditions." Tetrahedron 61, no. 35 (August 2005): 8423–42. http://dx.doi.org/10.1016/j.tet.2005.06.085.

Full text

APA, Harvard, Vancouver, ISO, and other styles

8

Pointner, Andreas, and Rudolf Herrmann. "Transition State Geometry and Solvent Effects in the Enantioselective Oxidation of Sulfides to Chiral Sulfoxides by Oxaziridines." Zeitschrift für Naturforschung B 50, no. 9 (September 1, 1995): 1396–403. http://dx.doi.org/10.1515/znb-1995-0917.

Full text

Abstract:

AbstractFor the enantioselective oxidation of methyl phenyl sulfide and tert-butyl methyl sulfide to the corresponding chiral sulfoxides by 3,3-dibromo-(camphorsulfonyl)oxaziridine, semiempirical calculations (MNDO, AMI, PM3) concerning transition state geometries were performed. The results show that only PM3 is able to localize a transition state. For methyl phenyl sulfide, a spiro arrangement of the oxaziridine ring and the sulfur atom explains the observed direction of the selectivity better than a planar transition state. The solvent dependence of the observed enantioselectivity is related to the calculated dipole moment of the transition state by the Kirkwood-Onsager model. In THF as solvent, its direct participation in the transition state has to be considered

APA, Harvard, Vancouver, ISO, and other styles

9

Dickmeis, Marcus, Hakan Cinar, and Helmut Ritter. "Macrocyclic and Polymeric Oxaziridine-Derivatives." Macromolecular Rapid Communications 34, no. 3 (January 11, 2013): 263–68. http://dx.doi.org/10.1002/marc.201200706.

Full text

APA, Harvard, Vancouver, ISO, and other styles

10

Singh, Santosh K., Jesse La Jeunesse, Cheng Zhu, N. Fabian Kleimeier, Kuo-Hsin Chen, Bing-Jian Sun, Agnes H. H. Chang, and Ralf I. Kaiser. "Gas phase identification of the elusive oxaziridine (cyclo-H2CONH) – an optically active molecule." Chemical Communications 56, no. 100 (2020): 15643–46. http://dx.doi.org/10.1039/d0cc06760a.

Full text

APA, Harvard, Vancouver, ISO, and other styles

More sources

Dissertations / Theses on the topic "Oxaziridine chemistry"

1

Albar, Hassan Abdulkader. "Studies on oxaziridines and 1,2,4-oxadiazoles." Thesis, Cardiff University, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.254499.

Full text

APA, Harvard, Vancouver, ISO, and other styles

2

Johnson, Graham P. "Mechanistic and synthetic aspects of the photochemistry of spiro-oxaziridines." Thesis, Loughborough University, 1986. https://dspace.lboro.ac.uk/2134/34395.

Full text

Abstract:

The photo-rearrangements of certain spiro-oxaziridines derived from tetral-1-one have been investigated in order to establish the effect of competition between aryl and alkyl migration and to examine the photochemistry of these systems when the N-substituent suffers steric compression. A range of spiro-oxaziridines having the N-substituent in the syn-aryl or anti-aryl configuration have been converted to the corresponding lactams, either as mixtures of regio-isomers or single substances. It has been demonstrated that stereo-electronically controlled photo-rearrangements (migration of the bond anti- to the lone-pair of electrons on the nitrogen atom) occur when the N-substituent is anti- to the aromatic ring. Reduced regio-specificity of the photo-rearrangement of syn-spiro-oxaziridines suggests that the first formed N–O bond cleaved species has a significant lifetime. The synthetic utility of the photo-rearrangement of the anti-aryl oxaziridine has been demonstrated by the preparation of a range of tricyclic, heterocyclic compounds, including pyrrolo-benzazepinones, pyrrolo-isoquinolinones and azeto-benzazepinones. The photo-products may have potential pharmacological activity.

APA, Harvard, Vancouver, ISO, and other styles

Book chapters on the topic "Oxaziridine chemistry"

1

Haddadin, Makhluf J., and Jeremiah P. Freeman. "Oxaziridines." In Chemistry of Heterocyclic Compounds: A Series Of Monographs, 283–350. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2008. http://dx.doi.org/10.1002/9780470187203.ch3.

Full text

APA, Harvard, Vancouver, ISO, and other styles

2

Davis, F. A., B. C. Chen, and P. Zhou. "Oxaziridines and Oxazirines." In Comprehensive Heterocyclic Chemistry III, 559–621. Elsevier, 2008. http://dx.doi.org/10.1016/b978-008044992-0.00112-7.

Full text

APA, Harvard, Vancouver, ISO, and other styles

3

Davis, Franklin A., and R. Thimma Reddy. "Oxaziridines and Oxazirines." In Comprehensive Heterocyclic Chemistry II, 365–413. Elsevier, 1996. http://dx.doi.org/10.1016/b978-008096518-5.00012-5.

Full text

APA, Harvard, Vancouver, ISO, and other styles

4

Woo, Sang Kook. "Oxaziridines and Oxazirines." In Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Elsevier, 2020. http://dx.doi.org/10.1016/b978-0-12-409547-2.14812-7.

Full text

APA, Harvard, Vancouver, ISO, and other styles

5

Lambert, Tristan H. "Construction of Single Stereocenters." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0037.

Full text

Abstract:

James L. Leighton at Columbia University reported (Nature 2012, 487, 86) that the commercially available allylsilane 2 allylated acetoacetone (1) to furnish the enantioenriched tertiary carbinol 3. Alexander T. Radosevich demonstrated (Angew. Chem. Int. Ed. 2012, 51, 10605) that diazaphospholidine 5 induced the formal reductive insertion of 3,5-dinitrobenzoic acid to α-ketoester 4 to generate adduct 6 enantioselectively. Tehshik P. Yoon at the University of Wisconsin at Madison found (J. Am Chem. Soc. 2012, 134, 12370) that aminoalcohol derivative 9 could be prepared via an asymmetric iron-catalyzed oxyamination of diene 7 using oxaziridine 8. A procedure for the desymmetrization of 1,3-difluoropropanol 10 by nucleophilic displacement of an unactivated aliphatic fluoride to generate 11 was reported (Angew. Chem. Int. Ed. 2012, 51, 12275) by Günter Haufe at the University of Münster and Norio Shibata at the Nagoya Institute of Technology. An innovative procedure for the amination of unactivated olefins involving an ene reaction/[ 2,3]-rearrangement sequence (e.g., 12 to 13) was developed (J. Am. Chem. Soc. 2012, 134, 18495) by Uttam K. Tambar at the University of Texas Southwestern Medical Center. James P. Morken at Boston College demonstrated the stereospecific amination of borane 14 with methoxylamine to produce 15. The conversion of β-ketoester 16 to 18 by amination with 17 under oxidative conditions was reported (J. Am. Chem. Soc. 2012, 134, 18948) by Javier Read de Alaniz at the University of California at Santa Barbara. The electrophilic amination of silyl ketene acetal 19 with a functionalized hydroxylamine reagent to produce 20 was disclosed (Angew. Chem. Int. Ed. 2012, 51, 11827) by Koji Hirano and Masahiro Miura at Osaka University. Erick M. Carreira at ETH Zürich developed (Angew. Chem. Int. Ed. 2012, 51, 8652) the enantioconvergent thioetherification of alcohol 21 to produce 23 with high branched to linear selectivity and ee. The asymmetric conjugate addition of 2-aminothiophenol 25 to 24 catalyzed by mesitylcopper in the presence of ligand 26 was developed (Angew. Chem. Int. Ed. 2012, 51, 8551) by Naoya Kumagai and Masakatsu Shibasaki at the Institute of Microbial Chemistry in Tokyo. The enantioselective conversion of aldehyde 28 to α-fluoride 30 under catalysis by NHC 29 was developed (Angew. Chem. Int. Ed. 2012, 51, 10359) by Zhenyang Lin and Jianwei Sun at the Hong Kong University of Science and Technology.

APA, Harvard, Vancouver, ISO, and other styles

We offer discounts on all premium plans for authors whose works are included in thematic literature selections. Contact us to get a unique promo code!