Kinetic Resolution of 2-N-Acylamido Tertiary Allylic Alcohols: Asymmetric Synthesis of Oxazolines
A series of cyclohexyl-fused SPINOL-derived phosphoric acids (Cy-SPA) have been developed to catalyze the kinetic resolution of 2-N-acylamido tertiary allylic alcohols, providing access to chiral oxazolines bearing C-2 alkyl substituents with high enantioselectivities (with s-factors up to 153). Gram-scale reaction with 1 mol% catalyst loading and transformations of the chiral products demonstrates the value of these methods. (Figure presented.).
Imidazolines substituted at the 1- and either the 4-, or 5-position with phenyl and at the 2-position with alkyl or phenyl have been prepared in racemic form. They appear to be fairly stable compounds and potentially useful as scaffolds in medicinal chemistry. Georg Thieme Verlag Stuttgart.
Lakner, Frederick J.,Parker, Matthew A.,Rogovoy, Boris,Khvat, Alexander,Ivachtchenko, Alexander
experimental part
p. 1987 - 1990
(2009/12/25)
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