title: Stereocontrolled formation of ketomethylene isosteres through tandem chain extension reactions.
abstract: A zinc-mediated chain extension reaction is the key step in the preparation of gamma-keto amides derived from amino acids. The use of tandem reaction sequences, in which the intermediate zinc enolate is trapped with electrophilic reagents, results in the incorporation of alpha-substituents, which mimic the side chains found in natural amino acid systems. Use of the chiral amino acid L-proline as a stereo-directing element provides a diastereoselective route to various ketomethylene isosteres.
authors.affiliation: Department of Chemistry, University of New Hampshire, Durham, New Hampshire 03824, USA.
authors.forename: Weimin
authors.initials: W
authors.lastname: Lin
authors.forename: Nancy
authors.initials: N
authors.lastname: Tryder
authors.forename: Fan
authors.initials: F
authors.lastname: Su
authors.forename: Charles K
authors.initials: CK
authors.lastname: Zercher
authors.forename: Jerry P
authors.initials: JP
authors.lastname: Jasinski
authors.forename: Ray J
authors.initials: RJ
authors.lastname: Butcher
mesh_terms: D007659:Ketones / Q000138:chemical synthesis*
chemical_list: D007659:Ketones