4.6 Article

Asymmetric borylation of alpha,beta-unsaturated esters catalyzed by novel ring expanded N-heterocyclic carbenes based on chiral 3,4-dihydro-quinazolinium compounds

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 34, Pages 6554-6556

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob01101e

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Funding

  1. Shanghai Municipal Education Commission [14ZZ159]
  2. Shanghai Municipal Science and Technology Commission [12430501300]
  3. Program for Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Education
  4. Start-up funding from Shanghai University of Engineering Science [E1-0501-14-0102]

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A series of chiral 6-membered ring N-heterocyclic carbene (NHC) precursors based on 3,4-dihydro-quinazoline were synthesized with overall yields of 54-62%. NHCs generated from these precursors show excellent asymmetric catalytic properties for borylation of alpha,beta-unsaturated esters with enantioselectivity of up to 93% with a catalyst content of only 1 mol%.

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