title: Entrapment and kinetic resolution of stabilized axial and equatorial conformers of spiro-β-lactams.
abstract: The facile synthesis of the stabilized axial and equatorial conformers of spiro-β-lactams was achieved via entrapment of cyclohexanone imines (Schiff bases) with acetoxyacetyl chloride in a [2 + 2]-cycloaddition reaction followed by their kinetic resolution. The immobilization of the racemic substrates on an inert solid support significantly reduced the reaction time and improved the enantioselectivity of conformers during kinetic resolution. The mechanism of the formation of the spiro-β-lactams was explored using B3LYP/6-31+G* level quantum chemical calculations.
authors.affiliation: Indian Institute of Integrative Medicine, Canal Road, Jammu, 180 001, J&K, India.
authors.forename: Naveen
authors.initials: N
authors.lastname: Anand
authors.forename: Bhahwal A
authors.initials: BA
authors.lastname: Shah
authors.forename: Munish
authors.initials: M
authors.lastname: Kapoor
authors.forename: Rajinder
authors.initials: R
authors.lastname: Parshad
authors.forename: Rattan L
authors.initials: RL
authors.lastname: Sharma
authors.forename: Maninder S
authors.initials: MS
authors.lastname: Hundal
authors.forename: Ajay P S
authors.initials: AP
authors.lastname: Pannu
authors.forename: Prasad V
authors.initials: PV
authors.lastname: Bharatam
authors.forename: Subhash C
authors.initials: SC
authors.lastname: Taneja
mesh_terms: D007097:Imines / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D012545:Schiff Bases / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D007097:Imines; D012545:Schiff Bases; D047090:beta-Lactams