41977-21-3Relevant articles and documents
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Ziffer,H. et al.
, p. 4048 - 4049 (1973)
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Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used in the synthesis of ampelomins and deoxy-carbasugars
Lagreca, María Eugenia,Carrera, Ignacio,Seoane, Gustavo A.,Brovetto, Margarita
, p. 853 - 856 (2014/02/14)
Stereoselective hydrogenation of methylcyclohex-2-ene-1,4-diols used as important intermediates for the preparation of ampelomins and deoxy-carbasugars was studied. These olefins were obtained in few steps from a chiral cis-diol resulting from microbial o
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.