4.6 Article

Asymmetric metal free beta-boration of alpha,beta-unsaturated imines assisted by (S)-MeBoPhoz

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 5, Pages 1328-1332

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob02478h

Keywords

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Funding

  1. Spanish Ministerio de Economia y Competitividad MINECO [CTQ2013-43395-P, CTQ2011-29054-C02-02, SEV-2013-0319]
  2. Generalitat de Catalunya [2014SGR409]
  3. ICIQ Foundation
  4. URV [2013PMF-PIPF-91]
  5. Durham University [2013PMF-PIPF-91]
  6. URV-ICIQ

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The adduct [MeO -> Bpin-Bpin](-) efficiently mediates the beta-boration of alpha,beta-unsaturated imines formed in situ. The use of chiral phosphines as additives, and in particular the chiral phosphine (S)-MeBoPhoz, enables the catalytic asymmetric reaction to proceed with higher enantioselectivity than the analogue copper(I) mediated reaction.

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