Issue 5, 2015
From the journal:

Organic & Biomolecular Chemistry

Asymmetric metal free β-boration of α,β-unsaturated imines assisted by (S)-MeBoPhoz†

Enrico La Cascia,ab   Xavier Sanz,ac   Carles Bo,c   Andrew Whiting*b  and  Elena Fernandez*a  

* Corresponding authors

a Department Química Física i Inorgànica, University Rovira i Virgili C/Marcellí Domingo s/n, Tarragona, Spain
E-mail: mariaelena.fernandez@urv.cat

b Centre for Sustainable Chemical Processes, Dept. of Chemistry, Durham University, South Road, Durham DH1 3LE, UK
E-mail: andy.whiting@durham.ac.uk

c ICIQ, Tarragona, Spain

Abstract

The adduct [MeO → Bpin–Bpin]− efficiently mediates the β-boration of α,β-unsaturated imines formed in situ. The use of chiral phosphines as additives, and in particular the chiral phosphine (S)-MeBoPhoz, enables the catalytic asymmetric reaction to proceed with higher enantioselectivity than the analogue copper(I) mediated reaction.

Graphical abstract: Asymmetric metal free β-boration of α,β-unsaturated imines assisted by (S)-MeBoPhoz

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Article information

DOI
https://doi.org/10.1039/C4OB02478H
Article type
Communication
Submitted
25 Nov 2014
Accepted
10 Dec 2014
First published
10 Dec 2014
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2015,13, 1328-1332

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Asymmetric metal free β-boration of α,β-unsaturated imines assisted by (S)-MeBoPhoz

E. L. Cascia, X. Sanz, C. Bo, A. Whiting and E. Fernandez, Org. Biomol. Chem., 2015, 13, 1328 DOI: 10.1039/C4OB02478H

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