Design, synthesis, and evaluation of a helicenoidal DMAP Lewis base catalyst

MR Crittall, HS Rzepa, DR Carbery - Organic Letters, 2011 - ACS Publications
MR Crittall, HS Rzepa, DR Carbery
Organic Letters, 2011ACS Publications
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.
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.
ACS Publications
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