Issue 25, 2006
From the journal:

Chemical Communications

Lithium amide conjugate addition for the asymmetric synthesis of 3-aminopyrrolidines

Stephen G. Davies,*a   A. Christopher Garner,a   Euan C. Goddard,a   Dennis Kruchinin,a   Paul M. Roberts,a   Humberto Rodriguez-Sollaa  and  Andrew D. Smitha  

* Corresponding authors

a Department of Organic Chemistry, University of Oxford, Chemical Research Laboratory, Mansfield Road, Oxford, UK
E-mail: steve.davies@chem.ox.ac.uk

Abstract

Conjugate addition of homochiral lithium amides to methyl 4-(N-benzyl-N-allylamino)but-2-enoate, chemoselective N-deprotection and concomitant cyclisation, followed by enolate functionalisation and deprotection allows access to syn- and anti-3,4-disubstituted aminopyrrolidines in > 98% d.e. and > 98% e.e.

Graphical abstract: Lithium amide conjugate addition for the asymmetric synthesis of 3-aminopyrrolidines

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Article information

DOI
https://doi.org/10.1039/B604835H
Article type
Communication
Submitted
04 Apr 2006
Accepted
28 Apr 2006
First published
18 May 2006

Chem. Commun., 2006, 2664-2666

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Lithium amide conjugate addition for the asymmetric synthesis of 3-aminopyrrolidines

S. G. Davies, A. C. Garner, E. C. Goddard, D. Kruchinin, P. M. Roberts, H. Rodriguez-Solla and A. D. Smith, Chem. Commun., 2006, 2664 DOI: 10.1039/B604835H

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