Reversal of Selectivity in Acetate Aldol Reactions of N-Acetyl-(S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one
Organic Letters2012Vol. 14(10), pp. 2442–2445
Citations Over TimeTop 10% of 2012 papers
Abstract
Synergistic effects of the exo- and endocyclic chiral centers of an imidazolidinone-based auxiliary were investigated in the perspective of acetate aldol reactions. The reversal in diastereoselectivity was accomplished by lithium and titanium enolate reactions, which proceed through proposed open and closed transitions states, respectively. The aldol adducts were used in the stereoselective synthesis of fluoxetine.
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