62875-07-4Relevant articles and documents
Hudson,Barker
, p. 3650,3658 (1967)
Enantioselective hydrolysis of functionalized 2,2-disubstituted oxiranes with bacterial epoxide hydrolases
Steinreiber, Andreas,Osprian, Ingrid,Mayer, Sandra F.,Orru, Romano V. A.,Faber, Kurt
, p. 3703 - 3711 (2007/10/03)
The biohydrolysis of 2,2-disubstituted oxiranes bearing various oxygen functional groups was investigated using the epoxide hydrolase activity of 11 bacterial strains. The results show that the activity and the selectivity strongly depend on the substrate structure and the biocatalyst. Whereas substrates possessing free hydroxyl groups were not transformed, their analogs, protected as ethers, were well accepted. This allowed the convenient modulation of the enantioselectivity by proper choice of the ether group according to size and polarity. It was found that the distance of the ether-oxygen to the stereogenic quaternary carbon center of the oxirane ring had a profound influence on the enantioselectivity, and several oxiranes were resolved with good to excellent selectivities. The enantiomerically enriched epoxides and vicinal diols thus obtained contain a useful 'synthetic handle' in their side chain, which allows their use as building blocks in asymmetric synthesis.
Regio- and Stereocontrolled Synthesis of Epoxy Alcohols and Triols from Allylic and Homoallylic Alcohols via Iodo Carbonates
Bongini, Alessandro,Cardillo, Giuliana,Orena, Mario,Porzi, Gianni,Sandri, Sergio
, p. 4626 - 4633 (2007/10/02)
The regio- and stereoselective synthesis of cyclic iodo carbonates 1-10, resulting from allylic and homoallylic alcohols was investigated.These useful intermediates were easily hydrolyzed to epoxy alcohols 11-20 or triols 21-30, depending on the polymeric reagent employed (Amberlyst A 26 in the OH- or CO32- form, respectively).Stereochemical assignments were carried out by 13C NMR or 1H NMR correlations and by conversion of the compounds to products of known stereostructures.