Reversal of selectivity in acetate aldol reactions of N-acetyl-(S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one

Organic Letters
Gopal L KhatikVipin A Nair

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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May 24, 2011·European Journal of Medicinal Chemistry·Gopal L KhatikVipin A Nair
Feb 14, 2012·Bioorganic & Medicinal Chemistry Letters·Gopal L KhatikVipin A Nair

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Citations

Sep 13, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Alba E Díaz-ÁlvarezPeter Dinér
Jul 17, 2013·Organic Letters·Digvijay GahtoryVipin A Nair
Oct 30, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marzena Wosińska-Hrydczuk, Jacek Skarżewski

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