General and stereoselective aminoxylation of biradical titanium(IV) enolates with TEMPO: a detailed study on the effect of the chiral auxiliary

Stuart C. D. Kennington; Alejandro Gómez-Palomino; Ernest Salomó; Pedro Romea; Fèlix Urpí; Mercè Font-Bardia

doi:10.1039/C8OB01074A

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

General and stereoselective aminoxylation of biradical titanium(iv) enolates with TEMPO: a detailed study on the effect of the chiral auxiliary†

Stuart C. D. Kennington,

^a Alejandro Gómez-Palomino,^a Ernest Salomó,^a Pedro Romea,

*^a Fèlix Urpí

*^a and Mercè Font-Bardia^b

Author affiliations

* Corresponding authors

^a Departament de Química Inorgànica i Orgànica, Secció de Química Orgànica, and Institut de Biomedicina (IBUB), Universitat de Barcelona, Carrer Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain
E-mail: pedro.romea@ub.edu, felix.urpi@ub.edu

^b Unitat de Difracció de RX. CCiTUB. Universitat de Barcelona, Carrer Solé i Sabarís 1-3, 08028 Barcelona, Catalonia, Spain

Abstract

A comprehensive analysis of the influence of the chiral auxiliary on the α-aminoxylation of titanium(IV) enolates with TEMPO indicated that (S) 4-tert-butyl-1-oxazolidine-2-thione is the most appropriate scaffold to provide a single diastereomer in high yields for a variety of substrates, which converts such a radical reaction into a highly chemo- and stereoselective oxidation.

This article is part of the themed collection: Synthetic methodology in OBC

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C8OB01074A
Article type: Paper
Submitted: 08 May 2018
Accepted: 13 Jun 2018
First published: 14 Jun 2018

Download Citation

Org. Biomol. Chem., 2018,16, 4807-4815

Permissions

Request permissions

General and stereoselective aminoxylation of biradical titanium(IV) enolates with TEMPO: a detailed study on the effect of the chiral auxiliary

S. C. D. Kennington, A. Gómez-Palomino, E. Salomó, P. Romea, F. Urpí and M. Font-Bardia, Org. Biomol. Chem., 2018, 16, 4807 DOI: 10.1039/C8OB01074A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic & Biomolecular Chemistry

General and stereoselective aminoxylation of biradical titanium(iv) enolates with TEMPO: a detailed study on the effect of the chiral auxiliary†

Abstract

Supplementary files

Article information

Download Citation

Permissions

General and stereoselective aminoxylation of biradical titanium(IV) enolates with TEMPO: a detailed study on the effect of the chiral auxiliary

Social activity

Search articles by author

Spotlight

Advertisements