Symmetric macrocycles by a Prins dimerization and macrocyclization strategy.
A tandem dimerization/macrocyclization reaction utilizing the Prins cyclization has been developed. This reaction develops molecular complexity through the formation of highly substituted dimeric tetrahydropyran macrocycles. Mild conditions utilizing rhenium(VII) catalysts were explored for aromatic substrates, while harsher Lewis acidic conditions were used for aliphatic substrates. Both aldehydes and acetals are shown to be viable substrates for this reaction.
Gesinski
Michael R
MR
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
Tadpetch
Kwanruthai
K
Rychnovsky
Scott D
SD
D002384:Catalysis; D003500:Cyclization; D019281:Dimerization; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012211:Rhenium / Q000737:chemistry; D013237:Stereoisomerism
D047028:Macrocyclic Compounds; D011714:Pyrans; D012211:Rhenium