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

Publication Type : Journal Article

Publisher : American Chemical Society

Source : Organic Letters, 2012

Url : https://pubs.acs.org/doi/full/10.1021/ol300949s?casa_token=Ggh-RbegenMAAAAA%3AceE-YwgvydSHqaBn0g1p4xRXqiVGQ5CbpEKpUD-K5k_C1fXcWIhx0meOBETnAACS_-vF1ShgqpDUQgWjTA

Campus : Amritapuri

School : School of Biotechnology

Year : 2012

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.

Cite this Research Publication : Gopal L. Khatik, Varun Kumar and Vipin A. Nair, "Reversal of selectivity in acetate aldol reactions of N-acetyl-(S)-4-isopropyl-1-[(R)-1-phenylethyl] imidazolidin-2-one", Organic Letters, 2012, 14, 2442-2445

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