title: Fluoroallylboration-olefination for the synthesis of (Z)-4,4-difluoropent-2-enoates and 5,5-difluoro-5,6-dihydropyran-2-ones.
abstract: Horner-Wadsworth-Emmons (HWE) or Still-Gennari olefination of TBS-protected 3,3-difluoro-4-hydroxy-2-ones, derived from the difluoroallylboration of aldehydes, provides the Z-isomer of 4,4,-difluoropent-2-enoates. These, upon hydrolysis, followed by Yamaguchi cyclization, afford 5,5-difluoro-4-methyl-5,6-dihydro-α-pyrones in high yields.
authors.affiliation: Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, United States. chandran@purdue.edu
authors.forename: P Veeraraghavan
authors.initials: PV
authors.lastname: Ramachandran
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Tafelska-Kaczmarek
authors.forename: Kaumba
authors.initials: K
authors.lastname: Sakavuyi
authors.forename: Anamitra
authors.initials: A
authors.lastname: Chatterjee
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D006845:Hydrocarbons, Fluorinated; D011753:Pyrones