4.8 Article

Design, Synthesis, and Evaluation of a Helicenoidal DMAP Lewis Base Catalyst

Journal

ORGANIC LETTERS
Volume 13, Issue 5, Pages 1250-1253

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol2001705

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Funding

  1. The University of Bath
  2. EPSRC [EP/E017495/1]
  3. Engineering and Physical Sciences Research Council [EP/E017495/1] Funding Source: researchfish
  4. EPSRC [EP/E017495/1] Funding Source: UKRI

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The design, synthesis, and study of a helical dialkylaminopyridine Lewis base catalyst is reported. Helical DMAP analogue 4 is based upon a helicenoid structure and displays good to excellent levels of selectivity (S <= 116) in the kinetic resolution of chiral secondary alcohols. Catalyst 4 displays excellent reactivity with exceptionally low loadings of 0.05 mol % effecting practical levels of selectivity in kinetic resolutions.

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