111768-08-2Relevant academic research and scientific papers
Systematic comparison of sets of 13C NMR spectra that are potentially identical. Confirmation of the configuration of a cuticular hydrocarbon from the cane beetle antitrogus parvulus
Basar, Norazah,Damodaran, Krishnan,Liu, Hao,Morris, Gareth A.,Sirat, Hasnah M.,Thomas, Eric J.,Curran, Dennis P.
, p. 7477 - 7490 (2014/10/15)
A systematic process is introduced to compare 13C NMR spectra of two (or more) candidate samples of known structure to a natural product sample of unknown structure. The process is designed for the case where the spectra involved can reasonably
Oxidations catalyzed by osmium compounds. Part 1: Efficient alkane oxidation with peroxides catalyzed by an olefin carbonyl osmium(0) complex
Shul'pin, Georgiy B.,Kudinov, Aleksandr R.,Shul'pina, Lidia S.,Petrovskaya, Elena A.
, p. 837 - 845 (2007/10/03)
A carbonyl osmium(0) complex with π-coordinated olefin, (2,3-η-1,4-diphenylbut-2-en-1,4-dione)undecacarbonyl triangulotriosmium (1), efficiently catalyzes oxygenation of alkanes (cyclohexane, cyclooctane, n-heptane, isooctane, etc.) with hydrogen peroxide, as well as with tert-butyl hydroperoxide and meta-chloroperoxybenzoic acid in acetonitrile solution. Alkanes are oxidized to corresponding alcohols, ketones (aldehydes) and alkyl hydroperoxides. Thus, heating cyclooctane with the 1-H2O2 combination at 70 °C gave products with turnover number as high as 2400 after 6 h. The maximum obtained yield of all products was equal to 20% based on cyclohexane and 30% based on H2O2. The oxidation of linear and branched alkanes exhibits very low regio- and bond-selectivity parameters and this testifies that the reaction proceeds via attack of hydroxyl radicals on C-H bonds of the alkane. The oxygenation products were not formed when the reaction was carried out under argon atmosphere and it can be thus concluded that the oxygenation occurs via the reaction between alkyl radicals and atmospheric oxygen. In summary, the Os(0) complex is much more powerful generator of hydroxyl radicals than any soluble derivative of iron (which is an analogue of osmium in the Periodic System).
Alkane oxygenation with H2O2 catalysed by FeCl 3 and 2,2′-bipyridine
Shul'pin, Georgiy B.,Golfeto, Camilla C.,Süss-Fink, Georg,Shul'pina, Lidia S.,Mandelli, Dalmo
, p. 4563 - 4567 (2007/10/03)
The H2O2-FeCl3-bipy system in acetonitrile efficiently oxidises alkanes predominantly to alkyl hydroperoxides. Turnover numbers attain 400 after 1 h at 60°C. It has been assumed that bipy facilitates proton abstraction from a H2O2 molecule coordinated to the iron ion (these reactions are stages in the catalytic cycle generating hydroxyl radicals from the hydrogen peroxide). Hydroxyl radicals then attack alkane molecules finally yielding the alkyl hydroperoxide.
Asymmetric conjugate addition for the preparation of syn-1,3-dimethyl arrays: Synthesis and structure elucidation of capensifuranone
Williams, David R.,Nold, Andrea L.,Mullins, Richard J.
, p. 5374 - 5382 (2007/10/03)
The synthesis of capensifuranone (1) has been achieved by the application of developments for asymmetric conjugate addition reactions of organocopper reagents with nonracemic N-enoyl-4-phenyl-1,3-oxazolidinones for the preparation of 1,3-syn-dimethyl arra
Toward a total synthesis of okilactomycin. 2. A metathesis-based approach to the heavily functionalized cyclohexane ring
Boulet, Serge L.,Paquette, Leo A.
, p. 895 - 900 (2007/10/03)
An attempt to access in an enantioselective fashion, a highly substituted cyclohexane as required for the northeastern sector of okilactomycin is described. The application of Oppolzer's sultam chemistry, involving in particular an optically and chemicall
Enantioselective carbometalation of cinnamyl derivatives: New access to chiral disubstituted cyclopropanes - Configurational stability of benzylic organozinc halides
Norsikian, Stephanie,Marek, Ilan,Klein, Sophie,Poisson, Jean F.,Normant, Jean F.
, p. 2055 - 2068 (2007/10/03)
A stoichiometric or catalytic amount of (-)-sparteine can serve asa promoter for the enantioselective carbolithiation of cinnamyl derivatives by primary and secondary organolithium compounds. The enantiofacial choice of the addition reaction is dependent on the stereochemistry of the initial double bond. The resulting benzylic organolithium compounds can be derivatized to a linear phenylated chain that bears two contiguous stereogenic centers with given configurations. The use of the dimethyl acetal of the (E)-cinnamyl alcohol allows the highest enantioselective carbolithiation and by simply warming the reaction mixture to room temperature, the resulting benzylic organo-lithium intermediate undergoes a 1,3-elimination to give the chiral disubstituted cyclopropane in high enantiomeric excess (90-95% ee). Another significant finding is the observation that the Li-Zn transmetalation in a benzylic species occurs with inversion of configuration, and the corresponding acyclic benzylic zinc halides have observable configurational stability at - 30°C.
Enantioselective carbolithiation of β-alkylated styrene
Norsikian, Stephanie,Marek, Ilane,Normant, Jean-F.
, p. 7523 - 7526 (2007/10/03)
Stoichiometric or catalytic amounts of (-) sparteine serve as promoter for enantioselective carbolithiation of β-alkylated, non functionalized styrene.
Sterically constrained tricyclic 2-oxazolidinone as excellent chiral auxiliary
Nakamura, Taiju,Hashimoto, Noriaki,Ishizuka, Tadao,Kunieda, Takehisa
, p. 559 - 562 (2007/10/03)
A new class of conformationally rigid 2-oxazolidinones with effectively bulky substituents, derived from the [4+2] cycloadduct of cyclopentadiene and a-oxazolone, serve as extremely powerful chiral auxiliaries for asymmetric alkylations, Diels-Alder reactions and conjugate addition reactions.
