title: Intermolecular Michael reactions: a computational investigation.
abstract: Computational studies have suggested that η(3)-lithium enolates in which the cation is partially bound to both carbon and oxygen may be important reactive intermediates. DFT calculations are used to demonstrate that explicitly solvated acetone enolates are largely O-bound. With this premise in mind, the stereochemical course of intermolecular Michael additions is examined. The results are generally consistent with what is observed experimentally and the model advanced by Heathcock and co-workers.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, United States. ekwan@fas.harVard.edu
authors.forename: Eugene E
authors.initials: EE
authors.lastname: Kwan
authors.forename: David A
authors.initials: DA
authors.lastname: Evans
mesh_terms: D002412:Cations; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002412:Cations; D009942:Organometallic Compounds; D008094:Lithium