4.7 Article

Chiral primary amine catalysed asymmetric conjugate addition of azoles to α-substituted vinyl ketones

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 1, Issue 1, Pages 68-72

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3qo00027c

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Funding

  1. Natural Science Foundation of China [21025208, 21202171]
  2. National Basic Research Program of China [2011CB808600]

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We report here the first effective example of asymmetric conjugate addition-protonation reactions of azoles to vinyl ketones by chiral primary amine catalysis. High enantioselectivity can be easily achieved by screening different primary amine catalysts, and the Curtin-Hammett control in the C-N bond formation step was verified by DFT calculations to account for the observed stereoselectivity.

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