Complex Boron-Containing Molecules through a 1,2-Metalate Rearrangement/anti-S N 2′ Elimination/Cycloaddition Reaction Sequence

Chloe Tillin, Raphael Bigler, Renata Calo-lapido, Beatrice Collins, Adam Noble, Varinder Aggarwal*

*Corresponding author for this work

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

3 Citations (Scopus)
413 Downloads (Pure)

Abstract

The three-component coupling of benzylamines, boronic esters, and 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione (PTAD) is reported. The boronate complex formed from an ortho-lithiated benzylamine and a boronic ester undergoes a stereospecific 1,2-metalate rearrangement/anti-S N 2′ elimination in the presence of an N-activator to provide a dearomatized tertiary boronic ester. Interception of this dearomatized intermediate with a dienophile leads to stereopredictable cycloaddition reactions to generate highly complex three-dimensional boron-containing molecular structures. When enantioenriched α-methyl-substituted benzylamines are employed, the corresponding cycloaddition adducts are formed with excellent enantiospecificities.
Original languageEnglish
Pages (from-to)449-453
Number of pages5
JournalSYNLETT
Volume30
Issue number4
Early online date20 Nov 2018
DOIs
Publication statusPublished - 1 Jan 2019

Keywords

  • cycloaddition
  • 1,2-metalate rearrangement
  • phenyltriazoledione
  • benzylamines
  • boronic esters
  • multicomponent reaction

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