Issue 52, 2014
From the journal:

Chemical Communications

Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols†‡

Olga Soares do Rego Barros,§a   Juan Alberto Sirvent,a   Francisco Foubelo*a  and  Miguel Yus*a  

* Corresponding authors

a Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
E-mail: foubelo@ua.es, yus@ua.es

Abstract

The palladium-catalyzed allylation of N-tert-butanesulfinyl imines with allylic alcohols in the presence of InI as reducing reagent takes place with high diastereoselectivity in reasonable yields. The reaction with crotyl alcohol is totally regioselective, leading to the anti-diastereomer as the main reaction product.

Graphical abstract: Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols

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Article information

DOI
https://doi.org/10.1039/C4CC02317J
Article type
Communication
Submitted
28 Mar 2014
Accepted
23 Apr 2014
First published
24 Apr 2014
This article is Open Access
Creative Commons BY license

Chem. Commun., 2014,50, 6898-6901

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Diastereoselective allylation and crotylation of N-tert-butanesulfinyl imines with allylic alcohols

O. S. D. R. Barros, J. A. Sirvent, F. Foubelo and M. Yus, Chem. Commun., 2014, 50, 6898 DOI: 10.1039/C4CC02317J

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