title: Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate.
abstract: A tandem chain extension-aldol reaction was developed in which beta-keto esters are transformed to alpha-substituted-gamma-keto esters in an efficient zinc-mediated, one-pot reaction. The diastereoselectivity of the reaction ranged from good to excellent with syn stereochemistry observed for beta-keto ester and amide substrates and anti-stereochemistry observed for a beta-keto imide. [reaction: see text]
authors.affiliation: Department of Chemistry, University of New Hampshire, Durham, NH 03824, USA.
authors.forename: S
authors.initials: S
authors.lastname: Lai
authors.forename: C K
authors.initials: CK
authors.lastname: Zercher
authors.forename: J P
authors.initials: JP
authors.lastname: Jasinski
authors.forename: S N
authors.initials: SN
authors.lastname: Reid
authors.forename: R J
authors.initials: RJ
authors.lastname: Staples
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D015032:Zinc