55156-13-3Relevant academic research and scientific papers
Benzannulation via ruthenium-catalyzed diol-diene [4+2] cycloaddition: One- and two-directional syntheses of fluoranthenes and acenes
Geary, Laina M.,Chen, Te-Yu,Montgomery, T. Patrick,Krische, Michael J.
, p. 5920 - 5922 (2014)
A new benzannulation protocol is described and applied to the synthesis of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol-diene [4+2] cycloaddition delivers cyclohex-1-ene-4,5-diols, which are subject to aromatization upon dehydration or Nicholas diol deoxydehydration. Employing diol and tetraol reactants, benzannulation can be conducted efficiently in one- and two-directional modes, respectively, as illustrated in the construction of substituted fluoranthenes and acenes.
Scope of the directed dihydroxylation: Application to cyclic homoallylic alcohols and trihaloacetamides
Donohoe, Timothy J.,Mitchell, Lee,Waring, Michael J.,Helliwell, Madeleine,Bell, Andrew,Newcombe, Nicholas J.
, p. 2173 - 2186 (2007/10/03)
The synthesis and directed dihydroxylation of a range of cyclic alkenes was investigated. Both homoallylic alcohols and homoallylic trihaloacetamides were found to be efficient directing groups, giving rise to good to excellent levels of remote asymmetric induction with OsO4-TMEDA. Interestingly, in all cases examined, trifluoroacetamides were found to be superior to trichloroacetamides as directing groups and an argument is presented which rationalises this observation.
On the stereoselectivity in bisdihydroxylation of 1,5-cyclooctadiene with osmium tetroxide
Kawazoe,Furusho,Nakanishi,Takata
, p. 2107 - 2112 (2007/10/03)
In the bisdihydroxylation of 1,5-cyclooctadiene with OsO4, use of a stoichiometric amount of OsO4 yielded a 1:1 mixture of syn- and anti-isomers, while use of a catalytic amount of OsO4 gave only syn-(1R*,2S*,5R*,6S*)-cyclooctane-1,2,5,6-tetrol. This syn-selectivity was attributed to the favorable formation of an intramolecular osmium(VI) bisglycolate ester in the catalytic reaction.
One-pot synthesis from 1,4-cyclohexadiene of (±)-1,4/2,5-cyclohexanetetrol, a naturally occurring cyclitol derivative
Maras, Ahmet,Erden, Mesut,Secen, Hasan,Suetbeyaz, Yasar
, p. 435 - 437 (2007/10/03)
SeO2-catalyzed direct hydroxylation of 1,4-cyclohexadiene with two molar equivalents of 30% H2O2 afforded (±)-1,4/2,5-cyclohexanetetrol, a naturally occurring cyclitol derivative, as the sole product in a good yield (88%).
