title: Reversal of selectivity in acetate aldol reactions of N-acetyl-(S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one.
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.
authors.affiliation: Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, Mohali, Punjab 160 062, India.
authors.forename: Gopal L
authors.initials: GL
authors.lastname: Khatik
authors.forename: Varun
authors.initials: V
authors.lastname: Kumar
authors.forename: Vipin A
authors.initials: VA
authors.lastname: Nair
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D005473:Fluoxetine / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry
chemical_list: D000447:Aldehydes; D007093:Imidazoles; C587749:N-acetyl-(S)-4-isopropyl-1-((R)-1-phenylethyl)imidazolidin-2-one; D005473:Fluoxetine; C116609:3-hydroxybutanal; D008094:Lithium; D014025:Titanium