Entrapment and Kinetic Resolution of Stabilized Axial and Equatorial Conformers of Spiro-β-lactams
The Journal of Organic Chemistry2011Vol. 76(15), pp. 5999–6006
Citations Over Time
Naveen Anand, Bhahwal Ali Shah, Munish Kapoor, Rajinder Parshad, Rattan L. Sharma, M.S. Hundal, A.P.S. Pannu, Prasad V. Bharatam, Subhash C. Taneja
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.
Related Papers
- → ChemInform Abstract: Synthesis of 4,4‐Bis(2‐methoxyethyl)cyclohexanone (IX) and of 4,4‐Bis‐( 2‐methoxyethyl)‐2‐cyclohexen‐1‐one (VIII).(1991)
- → ChemInform Abstract: Divergent Pathways of Reaction Between Cyclohexanone Enamines and . alpha.,β‐Unsaturated Acid Chlorides.(1996)
- → ChemInform Abstract: Enamine Chemistry. Part 29. Synthesis of Adamantane Derivatives from α,β‐Unsaturated Acid Chlorides and 4,4‐Disubstituted Cyclohexanone Enamines.(1986)
- → ChemInform Abstract: Polynuclear Heterocyclic Compounds from the Adduct of o‐Cinnamoylbenzoic Acid and Cyclohexanone.(1987)
- → ChemInform Abstract: Kinetic Resolution in the Directed Hydrogenation of N‐Substituted α‐(Aminoalkyl)acrylates, Precursors of Optically Active β‐Amino Acids.(1987)