title: Diastereoselective synthesis of tetrahydrofurans via Palladium(0)-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes and aldehydes.
abstract: Palladium(0)-catalyzed cycloadditions of malonate-derived vinylcyclopropane 1 and aldehydes to afford 2,5-cis disubstituted tetrahydrofuran derivatives are described. Pd loadings as low as 0.5 mol % were effective in catalyzing the transformation with high yields and diastereoselectivities. Electron-poor aldehydes work best, suggesting that a mechanism involving an initial aldol reaction may be operative.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
authors.forename: Andrew T
authors.initials: AT
authors.lastname: Parsons
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Campbell
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Johnson
mesh_terms: D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D003521:Cyclopropanes; D005663:Furans; D014753:Vinyl Compounds; D010165:Palladium