Synthesis of 3-Aryl-1-aminopropane Derivatives: Lithiation-Borylation-Ring-Opening of Azetidinium Ions

Giorgia Casoni, Eddie L. Myers, Varinder K Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

20 Citations (Scopus)
336 Downloads (Pure)

Abstract

In situ generated 2-phenyl-azetidinium ylides react with boronic esters to form acyclic γ-dimethylamino tertiary boronic esters. The transformation is believed to involve the formation of a zwitterionic boronate, which subsequently undergoes ring-opening 1,2-migration, which is promoted by the relief of ring strain. Owing to the configurational instability of the initially formed ylides, which appear to be in equilibrium with the open-chain carbene form, the reaction is not stereospecific. The C-B bond of the γ-dimethylamino tertiary boronic esters can be transformed into a variety of functional groups (C-OH, C-vinyl, C-H, C-BF3), thus giving a diverse selection of 3-aryl-1-aminopropanes, which represent a privileged motif among drug molecules.
Original languageEnglish
Pages (from-to)3241-3253
Number of pages13
JournalSynthesis (Germany)
Volume48
Issue number19
Early online date7 Jul 2016
DOIs
Publication statusPublished - 4 Oct 2016

Keywords

  • 3-aryl-1-aminopropanes
  • azetidinium ion
  • boronic esters
  • borylation
  • lithiation
  • ring-opening

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