Issue 4, 2009
From the journal:

Chemical Society Reviews

tert-Butanesulfinimines: structure, synthesis and synthetic applications

Franck Ferreira,*ab   Candice Botuha,ab   Fabrice Chemla*ab  and  Alejandro Pérez-Lunaab  

* Corresponding authors

a UPMC Univ Paris 06, UMR 7611, Laboratoire de Chimie Organique, Institut de Chimie Moléculaire (FR 2769), case 183, 4 place Jussieu, Paris, France
E-mail: franck.ferreira@upmc.fr, fabrice.chemla@upmc.fr
Fax: +33 (1) 44277567
Tel: +33 (1) 44275571

b CNRS, UMR 7611, Laboratoire de Chimie Organique, Institut de Chimie Moléculaire (FR 2769), case 183, 4 place Jussieu, Paris, France

Abstract

Since Ellman’s seminal works, over the past ten years tert-butanesulfinimines have proved to be useful chiral amino intermediates for organic synthesis. Through highly stereoselective reactions, amongst which reductions, nucleophilic 1,2-additions and ylide condensations, a broad range of nitrogen-containing compounds has been synthesized. Although the stereoselectivity levels are high in most cases, the sense of the stereoinduction is generally not predictable. The object of this critical review is to present the models proposed to rationalize the stereochemical outcome of the reactions involving tert-butanesulfinimines and to point out an obvious lack of homogeneity amongst them (128 references).

Graphical abstract: tert-Butanesulfinimines: structure, synthesis and synthetic applications

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Article information

DOI
https://doi.org/10.1039/B809772K
Article type
Critical Review
Submitted
21 Jul 2008
First published
26 Jan 2009

Chem. Soc. Rev., 2009,38, 1162-1186

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tert-Butanesulfinimines: structure, synthesis and synthetic applications

F. Ferreira, C. Botuha, F. Chemla and A. Pérez-Luna, Chem. Soc. Rev., 2009, 38, 1162 DOI: 10.1039/B809772K

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