6261-35-4Relevant 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.
supporting information, p. 5920 - 5922 (2014/05/20)
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.
Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenative [4+2] cycloaddition
Kasun, Zachary A.,Geary, Laina M.,Krische, Michael J.
supporting information, p. 7545 - 7547 (2014/07/07)
A new method for the ring expansion of cyclic diols is described. Using improved conditions for the ruthenium(0) catalyzed cycloaddition of cyclic 1,2-diols with 1,3-dienes, fused [n.4.0] bicycles 3a-3r (n = 3-6) are formed, which upon exposure to iodosobenzene diacetate engage in oxidative cleavage to form the 9-12 membered rings 4a-4r. the Partner Organisations 2014.
Ring opening of epoxides with NaHSO4: isolation of β-hydroxy sulfate esters and an effective synthesis for trans-diols
Cavdar, Huseyin,Saracoglu, Nurullah
experimental part, p. 985 - 989 (2009/04/07)
Sodium hydrogen sulfate (NaHSO4) was observed to be highly effective as a reagent or catalyst in the ring-opening reactions of epoxides under mild conditions. Reaction of epoxides with NaHSO4 gave isolable β-hydroxy sulfate esters and vicinal diols. Experimenting with different epoxides, the study investigated the scope of the ring-opening reaction.
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%).
