39789-20-3Relevant articles and documents
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.
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