Lithium Amide Conjugate Addition for the Asymmetric Synthesis of 3-Aminopyrrolidines

Stephen G. Davies, A. Christopher Garner, Euan C. Goddard, Dennis Kruchinin, Paul M. Roberts, Humberto Rodriguez-Solla, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2664-2666
Number of pages3
JournalChemical Communications
Issue number25
DOIs
Publication statusPublished - 2006

Keywords

  • 1,3-DIPOLAR CYCLOADDITION
  • GLYCOSIDASE INHIBITORS
  • AMMONIA EQUIVALENTS
  • KINETIC PROTONATION
  • ACIDS
  • STEREOCHEMISTRY
  • DERIVATIVES
  • AGENTS

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