Issue 79, 2012
From the journal:

Chemical Communications

Chemo- and enantioselective Rh-catalysed hydrogenation of 3-methylene-1,2-diazetidines: application to vicinal diamine synthesis†

Greg P. Iacobini,a   David W. Porterb  and  Michael Shipman*a  

* Corresponding authors

a Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, UK
E-mail: m.shipman@warwick.ac.uk
Fax: +44 (0)2476 524112
Tel: +44 (0)2476 523186

b Novartis Institutes for BioMedical Research, Wimblehurst Road, Horsham Research Centre, West Sussex, UK

Abstract

Rhodium catalysed hydrogenation of 3-methylene-1,2-diazetidines with a range of chiral ligands is reported. Using Mandyphos, excellent levels of chemo- and enantioselectivity (up to 89% ee) can be achieved. Reductive cleavage of the derived 3-substituted 1,2-diazetidine with LiDBB provides the enantioenriched biscarbamate protected 1,2-diamine.

Graphical abstract: Chemo- and enantioselective Rh-catalysed hydrogenation of 3-methylene-1,2-diazetidines: application to vicinal diamine synthesis

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Article information

DOI
https://doi.org/10.1039/C2CC35445D
Article type
Communication
Submitted
27 Jul 2012
Accepted
17 Aug 2012
First published
20 Aug 2012

Chem. Commun., 2012,48, 9852-9854

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Chemo- and enantioselective Rh-catalysed hydrogenation of 3-methylene-1,2-diazetidines: application to vicinal diamine synthesis

G. P. Iacobini, D. W. Porter and M. Shipman, Chem. Commun., 2012, 48, 9852 DOI: 10.1039/C2CC35445D

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