Jump to main content
Jump to site search

Issue 12, 2007
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Additions and corrections

Publication details

The article was received on 02 Apr 2007, accepted on 08 May 2007 and first published on 17 May 2007


Article type: Paper
DOI: 10.1039/B704932C
Citation: Org. Biomol. Chem., 2007,5, 1961-1969
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements