Copper-Catalyzed Borylation of Cyclic Sulfamidates: Access to Enantiomerically Pure (β-and γ-Amino-alkyl)boronic Esters

Nina Ursinyova, Robin B Bedford, Timothy Gallagher*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

10 Citations (Scopus)
333 Downloads (Pure)

Abstract

Cyclic sulfamidates undergo borylation under copper-catalyzed conditions using B2pin2 to give enantiomerically (and diasteromerically) defined aminoalkyl boronic esters. Extraneous iodide is essential but the intermediacy of simple alkyl iodides has been excluded; N-sulfated intermediates are key in the borylation sequence. Based on stereochemical studies and trapping experiments, the involvement of carbon-centered radicals under these copper-catalyzed conditions appears likely.
Original languageEnglish
Pages (from-to)673-677
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number4
Early online date23 Dec 2015
DOIs
Publication statusPublished - 5 Feb 2016

Structured keywords

  • BCS and TECS CDTs

Keywords

  • (Aminoalkyl)boronic esters
  • Boron
  • Copper
  • Cyclic sulfamidates
  • Radical reactions

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