title: Catalytic asymmetric synthesis of hydroxy enol ethers: approach to a two-carbon homologation of aldehydes.
abstract: [reaction: see text] Hydroboration of ethoxy acetylene, transmetalation to zinc, and addition to aldehydes in the presence of a chiral amino alcohol ligand (MIB) affords hydroxy enol ethers with high ee. The resultant enantiomerically enriched hydroxy enol ethers were converted to protected hydroxy aldehydes, a useful synthetic building block for the construction of a variety of polyoxygenated natural products. In addition, diastereoselective formation of syn- and anti-1,3-diols was studied.
authors.affiliation: Department of Chemistry, P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
authors.forename: Sang-Jin
authors.initials: SJ
authors.lastname: Jeon
authors.forename: Young K
authors.initials: YK
authors.lastname: Chen
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh