Issue 93, 2012
From the journal:

Chemical Communications

Novel transformation of α,β-unsaturated aldehydes and ketones into γ-amino alcohols or 1,3-oxazines via a 4 or 5 step, one-pot sequence†

Adam D. J. Calow,a   Andrei S. Batsanov,a   Elena Fernández,*b   Cristina Soléb  and  Andrew Whiting*a  

* Corresponding authors

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

b Dept. Química Física i Inorgànica, Universitat Rovira I Virgili, 43007 Tarragona, Spain

Abstract

An efficient, 4-step, one-pot, highly stereoselective route to γ-amino alcohols has been developed via an in situ α,β-unsaturated imine formation, β-boration, reduction (C[double bond, length as m-dash]N) and oxidation (C–B) sequence and especially for certain water-soluble γ-amino alcohols, a further step can be added to directly access the corresponding 1,3-oxazine derivatives.

Graphical abstract: Novel transformation of α,β-unsaturated aldehydes and ketones into γ-amino alcohols or 1,3-oxazines via a 4 or 5 step, one-pot sequence

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Article information

DOI
https://doi.org/10.1039/C2CC36129A
Article type
Communication
Submitted
23 Aug 2012
Accepted
20 Sep 2012
First published
24 Sep 2012

Chem. Commun., 2012,48, 11401-11403

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Novel transformation of α,β-unsaturated aldehydes and ketones into γ-amino alcohols or 1,3-oxazines via a 4 or 5 step, one-pot sequence

A. D. J. Calow, A. S. Batsanov, E. Fernández, C. Solé and A. Whiting, Chem. Commun., 2012, 48, 11401 DOI: 10.1039/C2CC36129A

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