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Literature DB >> 21076655

N-Nosyl Oxaziridines as Terminal Oxidants in Copper(II)-Catalyzed Olefin Oxyaminations.

Sandra M Deporter¹, Ashley C Jacobsen, Katherine M Partridge, Kevin S Williamson, Tehshik P Yoon.

Abstract

We report that N-4-nosyl-3-phenyloxaziridine is an effective terminal oxidant for copper(II)-catalyzed oxyamination recently developed in our labs. This oxaziridine can be prepared on multi-gram scale and is easily purified by recrystallization. The products of oxyamination using this oxaziridine bear protecting groups that can be readily removed in high yields under mild conditions.

Entities: Chemical Disease

Year: 2010 PMID： 21076655 PMCID： PMC2976543 DOI： 10.1016/j.tetlet.2010.08.015

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

18 in total

1. Copper(II)-catalyzed aminohydroxylation of olefins.

Authors: David J Michaelis; Christopher J Shaffer; Tehshik P Yoon
Journal: J Am Chem Soc Date: 2007-01-30 Impact factor: 15.419

2. Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and S(N)2 C-O bond formation.

Authors: Guosheng Liu; Shannon S Stahl
Journal: J Am Chem Soc Date: 2006-06-07 Impact factor: 15.419

3. A metal-free approach to the synthesis of indoline derivatives by a phenyliodine(III) bis(trifluoroacetate)-mediated amidohydroxylation reaction.

Authors: Arkaitz Correa; Imanol Tellitu; Esther Domínguez; Raul SanMartin
Journal: J Org Chem Date: 2006-10-13 Impact factor: 4.354

N-Nosyl Oxaziridines as Terminal Oxidants in Copper(II)-Catalyzed Olefin Oxyaminations.

1. Copper(II)-catalyzed aminohydroxylation of olefins.

2. Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and S(N)2 C-O bond formation.

3. A metal-free approach to the synthesis of indoline derivatives by a phenyliodine(III) bis(trifluoroacetate)-mediated amidohydroxylation reaction.

4. A new general method for the preparation of N-sulfonyloxaziridines.

5. Bronsted acid-promoted olefin aziridination and formal anti-aminohydroxylation.

6. tert-Butylsulfonyl (Bus), a New Protecting Group for Amines.

7. Palladium(II)-catalyzed aerobic dialkoxylation of styrenes: a profound influence of an o-phenol.

8. Palladium-catalyzed ring-forming aminoacetoxylation of alkenes.

9. Copper(I) catalysed cyclisation of unsaturated N-benzoyloxyamines: an aminohydroxylation via radicals.

10. Novel Pd(II)-catalysed N,O-bicyclisation as an efficient route to the 6-oxa-2-azabicyclo[3.2.1]octane skeleton.

1. Directed, Palladium(II)-Catalyzed Intermolecular Aminohydroxylation of Alkenes Using a Mild Oxidation System.

2. Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F.

3. Iron catalyzed asymmetric oxyamination of olefins.

Review 4. Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines.