39789-20-3Relevant academic research and scientific papers
Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides
Cresswell, Alexander J.,Davies, Stephen G.,Figuccia, Aude L.A.,Fletcher, Ai M.,Heijnen, Dorus,Lee, James A.,Morris, Melloney J.,Kennett, Alice M.R.,Roberts, Paul M.,Thomson, James E.
supporting information, p. 3373 - 3377 (2015/06/02)
The incorporation of alkoxy ligands within a range of alkoxyfluoroboranes and dialkoxyfluoroboranes results in fluoroborane reagents with attenuated Lewis acidity and increased ability to donate fluoride ion(s) when compared to boron trifluoride itself. Pinacolatoboron fluoride (pinBF), prepared in situ from BF3·OEt2 and bis(O-trimethylsilyl)pinacol, has been identified as an efficient fluoride donor which allows highly stereoselective SN1-type epoxide ring-opening (with retention of configuration) of a range of trans-β-methyl-substituted aryl epoxides to give the corresponding syn-fluorohydrins. The substrate scope of this transformation is more broad than the analogous protocol using boron trifluoride alone.
Palladium-catalyzed silylation of alcohols with hexamethyldisilane
Shirakawa, Eiji,Hironaka, Koji,Otsuka, Hidehito,Hayashi, Tamio
, p. 3927 - 3929 (2007/10/03)
The combination of hexamethyldisilane and a catalytic amount of [PdCl(η3-C3H5)]2-PPh 3 was found to be effective for the trimethylsilylation of alcohols, where both of the two trimethylsilyl groups of hexamethyldisilane were transferred to alcohols without coproduction of any stoichiometric amount of byproduct but H2. The Royal Society of Chemistry 2006.
Why Are Silyl Ethers Conformationally Different from Alkyl Ethers? Chair-Chair Conformational Equilibria in Silyloxycyclohexanes and Their Dependence on the Substituents on Silicon. The Wider Roles of Eclipsing, of 1,3-Repulsive Steric Interactions, and o
Marzabadi, Cecilia H.,Anderson, J. Edgar,Gonzalez-Outeirino, Jorge,Gaffney, Piers R. J.,White, Christopher G. H.,Tocher, Derek A.,Todaro, Louis J.
, p. 15163 - 15173 (2007/10/03)
An NMR study of the diaxial/diequatorial chair equilibrium in a range of silylated derivatives of trans-1,4- and trans-1,2-dihydroxycyclohexane is reported and discussed with a view to explaining unusually large populations of chair conformations with axi
Enantiodifferentiating Functionalization of cis-Cycloalkane-1,2-diols and cis-endo-5-Norbornen-2,3-ylenebis(methanol) via Chiral Spiroacetals Derived from 1-Menthone
Harada, Toshiro,Wada, Isao,Oku, Akira
, p. 2599 - 2605 (2007/10/02)
The enantiodifferentiating transformation of a prochiral hydroxyl group in cis-cycloalkane-1,2-diols and cis-endo-5-norbornen-2,3-ylenebis(methanol) (16) is presented.The reactions of the bis(trimethylsilyl) derivatives of 1,2-diols 6a-d with l-menthone i
A FACILE SYNTHESIS OF 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSYLIDENE ACETALS USING TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE CATALYST
Yoshimura, Juji,Horito, Shigeomi,Hashimoto, Hironobu
, p. 375 - 376 (2007/10/02)
The application of acetalization of aldehydes and ketones by alkoxysilanes in the presence of trimethylsilyl trifluoromethanesulfonate catalyst to lactones and di-O-trimethylsilyl-α-diols gave readily the corresponding spiro ortho esters.
