Issue 12, 2007
From the journal:

Organic & Biomolecular Chemistry

Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidinesvia lithium amide conjugate addition†

Stephen G. Davies,*a   A. Christopher Garner,a   Euan C. Goddard,a   Dennis Kruchinin,a   Paul M. Roberts,a   Andrew D. Smith,a   Humberto Rodriguez-Solla,a   James E. Thomsona  and  Steven M. Tomsa  

* Corresponding authors

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

Abstract

The diastereoselective conjugate addition of homochiral lithium amides to methyl 4-(N-allyl-N-benzylamino)but-2-enoate has been used as the key step in a simple and efficient protocol for the preparation of 3,4-substituted aminopyrrolidines. This protocol provides a complementary and stereoselective route to both anti- and syn-3-amino-4-alkylpyrrolidines as well as anti- and syn-3-hydroxy-4-aminopyrrolidines, in high de and ee via β-amino enolate functionalisation. This methodology has been applied to the synthesis of anti-(3S,4S)- and syn-(3R,4S)-3-methoxy-4-(N-methylamino)pyrrolidine.

Graphical abstract: Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidinesvia lithium amide conjugate addition

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Article information

DOI
https://doi.org/10.1039/B704932C
Article type
Paper
Submitted
02 Apr 2007
Accepted
08 May 2007
First published
17 May 2007

Org. Biomol. Chem., 2007,5, 1961-1969

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Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidinesvia lithium amide conjugate addition

S. G. Davies, A. C. Garner, E. C. Goddard, D. Kruchinin, P. M. Roberts, A. D. Smith, H. Rodriguez-Solla, J. E. Thomson and S. M. Toms, Org. Biomol. Chem., 2007, 5, 1961 DOI: 10.1039/B704932C

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