41977-22-4Relevant articles and documents
A Change from Kinetic to Thermodynamic Control Enables trans-Selective Stereochemical Editing of Vicinal Diols
Gu, Xin,Wendlandt, Alison E.,Zhang, Yu-An
supporting information, p. 599 - 605 (2022/01/03)
Here, we report the selective, catalytic isomerization of cis-1,2-diols to trans-diequatorial-1,2-diols. The method employs triphenylsilanethiol (Ph3SiSH) as a catalyst and proceeds under mild conditions in the presence of a photoredox catalyst and under
Synthesis and reactions of enantiopure substituted benzene cis-hexahydro-1,2-diols
Boyd,Sharma,Berberian,Dunne,Hardacre,Kaik,Kelly,Malone,McGregor,Stevenson
experimental part, p. 855 - 868 (2010/07/05)
Enantiopure dis-dihydro-1,2-diol metabolites, obtained from toluene dioxygenase-catalysed dis-dihydroxylation of six monosubstituted benzene substrates, have been converted to their corresponding dis-hexahydro-1,2-diol derivatives by catalytic hydrogenation via their dis-tetrahydro-1,2-diol intermediates. Optimal reaction conditions for total catalytic hydrogenation of the dis-dihydro-1,2-diols have been established using six heterogeneous catalysts. The relative and absolute configurations of the resulting benzene dis-hexahydro-1,2-diol products have been unequivocally established by X-ray crystallography and NMR spectroscopy. Methods have been developed to obtain enantiopure dis-hexahydro-1,2diol diastereoisomers, to desymmetrise a meso-cishexahydro-1,2-diol and to synthesise 2-substituted cyclohexanols. The potential of these enantiopure cyclohexanols as chiral reagents was briefly evaluated through their application in the synthesis of two enantiomerically enriched phosphine oxides from the corresponding racemic phosphine precursors.
The Use of Bismuth(III) Acetate in 'Wet' and 'Dry' Prevost Reactions
Trainor, Robert W.,Deacon, Glen B.,Jackson, W. Roy,Giunta, Nunzio
, p. 1265 - 1280 (2007/10/02)
cis-Diol and trans-diol derivatives can be prepared from alkenes by reaction with iodine and bismuth(III) acetate in 'wet' and 'dry' acetic acid, respectively.Reactions using lesser amounts of bismuth(III) acetate under 'dry' conditions give iodo acetates and under 'wet' conditions a mixture of iodohydrins and iodo ethers.Comparison of these reactions with those promoted by silver, copper, mercury and thallium salts is included.