Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration

Veronika M. Shoba, Nathan C. Thacker, Andrew J. Bochat, James M. Takacs

Research output: Contribution to journalArticle

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Abstract

Chiral boronic esters are useful intermediates in asymmetric synthesis. We have previously shown that carbonyl-directed catalytic asymmetric hydroboration (CAHB) is an efficient approach to the synthesis of functionalized primary and secondary chiral boronic esters. We now report that the oxime-directed CAHB of alkyl-substituted methylidene and trisubstituted alkene substrates by pinacolborane (pinBH) affords oxime-containing chiral tertiary boronic esters with yields up to 87 % and enantiomeric ratios up to 96:4 e.r. The utility of the method is demonstrated by the formation of chiral diols and O-substituted hydroxylamines, the generation of quaternary carbon stereocenters through carbon-carbon coupling reactions, and the preparation of chiral 3,4,4-trisubstituted isoxazolines.

Original languageEnglish (US)
Pages (from-to)1465-1469
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number4
DOIs
StatePublished - Jan 22 2016

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Keywords

  • asymmetric catalysis
  • homogeneous catalysis
  • hydroboration
  • oximes
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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