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

Gopal L Khatik; Varun Kumar; Vipin A Nair

doi:10.1021/ol300949s

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

Org Lett. 2012 May 18;14(10):2442-5. doi: 10.1021/ol300949s. Epub 2012 May 9.

Authors

Gopal L Khatik¹, Varun Kumar, Vipin A Nair

Affiliation

¹ Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, Mohali, Punjab 160 062, India.

PMID: 22571237
DOI: 10.1021/ol300949s

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Fluoxetine / chemical synthesis*
Fluoxetine / chemistry
Imidazoles / chemical synthesis
Imidazoles / chemistry*
Lithium / chemistry
Molecular Structure
Stereoisomerism
Titanium / chemistry

Substances

Aldehydes
Imidazoles
N-acetyl-(S)-4-isopropyl-1-((R)-1-phenylethyl)imidazolidin-2-one
Fluoxetine
3-hydroxybutanal
Lithium
Titanium