38036-63-4Relevant articles and documents
Desymmetrization of meso-Hydrobenzoin Using Chiral, Nucleophilic Phosphine Catalysts
Vedejs,Daugulis,Tuttle
, p. 1389 - 1392 (2004)
The desymmetrization of meso-hydrobenzoin is described using chiral phosphine catalysts 8b-d and 9-11. The best enantioselectivity at room temperature was obtained with the newly synthesized phospholane 8c and benzoic anhydride, but the reaction is very s
Reduction of diesters of 1,2-diols. Regioselective C-O bond cleavage of the anionic forms
Macias-Ruvalcaba, Norma A.,Moy, Cheryl L.,Zheng, Zi-Rong,Evans, Dennis H.
, p. 4829 - 4834 (2007/10/03)
The electrochemical reduction of benzoate diesters of glycols has been studied in acetonitrile and N,N-dimethylformamide as solvents. The reductions occur in two closely spaced one-electron steps, and it was found that the dianion diradicals decompose by one of two routes, depending on the substituents on the ethylene moiety: cleavage of two benzoates to produce alkene or formation of benzil by way of a postulated cyclic intermediate to produce also the dianion of the diol. These correspond to cleavage of the R-OC(O)Ar bonds and the RO-C(O)Ar bonds, respectively. When the radical formed by the former cleavage is a primary or secondary radical, the reaction is too slow to compete with the latter reaction that produces benzil. However, when that radical is either tertiary or benzylic, the former cleavage reaction is fast and no benzil is detected. The dianions of p-cyano- and p-nitrobenzoate esters are rather stable on the voltammetric time scale. However, the addition of lithium ions results in detectable formation of 4,4′-dicyanobenzil from four different p-cyanobenzoate diesters.
Highly efficient catalytic asymmetric acylation of meso-1,2-diols with benzoyl chloride in the presence of a chiral diamine combined with Et3N
Oriyama, Takeshi,Imai, Keisuke,Sano, Tomohumi,Hosoya, Takeshi
, p. 3529 - 3532 (2007/10/03)
Catalytic asymmetric acylation of meso-1,2-diols has been successfully performed by the reaction with benzoyl chloride in the presence of 0.5 mol% of chiral diamine derived from (S)-proline combined with a stoichiometric amount of triethylamine to give th
