Diastereoselective synthesis of tetrahydrofurans via Palladium(0)-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes and aldehydes.
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.
Parsons
Andrew T
AT
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
Campbell
Matthew J
MJ
Johnson
Jeffrey S
JS
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*
D003521:Cyclopropanes; D005663:Furans; D014753:Vinyl Compounds; D010165:Palladium