Gem-difluorinated homoallyl alcohols, beta-hydroxy ketones, and syn- and anti-1,3-diols via gamma,gamma-difluoroallylboronates.
Gamma,gamma-difluoroallylboronates have been prepared from trifluoroethanol and utilized for the allylboration of a variety of aldehydes to provide gem-difluorinated homoallylic alcohols. Alpha-chiral aldehydes were allylborated in 4:1-13:1 diastereoselectivity favoring the anti-isomer. A representative series of difluorinated hydroxyl enol ethers were converted to the corresponding alpha,alpha-difluoro-beta-hydroxy ketones. Diastereoselective reduction of one of these to either syn- and anti-1,3-diol was also studied.
Ramachandran
P Veeraraghavan
PV
Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA. chandran@purdue.edu
Chatterjee
Anamitra
A
D001897:Boronic Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007659:Ketones / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
D001897:Boronic Acids; D007659:Ketones; D020005:Propanols; C006463:allyl alcohol