166376-77-8Relevant academic research and scientific papers
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.
Asymmetric desymmetrization of saturated and unsaturated meso-1,2-diols
Fujioka, Hiromichi,Nagatomi, Yasushi,Kotoku, Naoyuki,Kitagawa, Hidetoshi,Kita, Yasuyuki
, p. 10141 - 10151 (2007/10/03)
An asymmetric desymmetrization of saturated and unsaturated cyclic and acyclic meso-1,2-diols has been developed from the ene acetals, prepared from the norbornene carboxyaldehyde and meso-1,2-diols. The intramolecular haloetherification of the ene acetals as a key step afforded 8-membered acetals in a stereoselective manner just by the reaction of norbornene olefin even when the ene acetals from unsaturated meso-1,2-diols having olefins in the same molecule were used. Subsequent reductive elimination, followed by protecting the hydroxy group and transacetalization, gave optically active 1,2-diol derivatives and the starting ene acetals in good yields. (C) 2000 Elsevier Science Ltd.
Preparation and Enantiomer Recognition Behaviour of Azophenolic Crown Ethers containing cis-Cyclohexane-1,2-diol as a Chiral Centre
Naemura, Koichiro,Takeuchi, Sachiko,Hirose, Keiji,Tobe, Yoshito,Kaneda, Takahiro,Sakata, Yoshiteru
, p. 213 - 220 (2007/10/02)
Both enentiomers of the azophenolic crown ether 1 incorporating the cis-cyclohexane-1,2-diol residue as the chiral centre have been prepared in enantiomerically pure forms and the chiral recognition behaviour towards 2-aminoethanols and ethylamines has be
