2396-76-1Relevant academic research and scientific papers
Dihydroxylation of olefins catalyzed by zeolite-confined osmium(0) nanoclusters: An efficient and reusable method for the preparation of 1,2-cis-diols
Metin, Oender,Alp, Nurdan Alcan,Akbayrak, Serdar,Bier, Abdullah,Gueltekin, Mehmet Serdar,Oezkar, Saim,Bozkaya, Uur
experimental part, p. 1488 - 1492 (2012/06/29)
Addressed herein is a novel, eco-friendly, recoverable, reusable and bottleable catalytic system developed for the dihydroxylation of various olefins yielding 1,2-cis-diols. In our protocol, zeolite-confined osmium(0) nanoclusters (zeolite-Os0) are used as reusable catalyst and H 2O2 served as a co-oxidant. Zeolite-Os0 are found to be highly efficient and selective catalysts for the dihydroxylation of a wide range olefins in an aqueous acetone mixture at room temperature. In all of the olefins surveyed, the catalytic dihydroxylation reaction proceeds smoothly and the corresponding 1,2-cis-diols are obtained in excellent chemical yield under the optimized conditions. The present heterogeneous catalyst system provides many advantages, such as being eco-friendly and industrially applicable over the traditional homogenous OsO4-NMO system for the dihydroxylation of olefins.
Triflic acid catalyzed oxidative lactonization and diacetoxylation of alkenes using peroxyacids as oxidants
Kang, Yan-Biao,Gade, Lutz H.
experimental part, p. 1610 - 1615 (2012/04/04)
A clean and efficient diacetoxylation reaction of alkenes catalyzed by triflic acid using commercially available peroxyacids as the oxidants has been developed. This method was also applied in oxidative lactonizations of unsaturated carboxylic acids in good to high yields.
A multicatalyst system for the one-pot desymmetrization/oxidation of meso-1,2-alkane diols
Mueller, Christian E.,Hrdina, Radim,Wende, Raffael C.,Schreiner, Peter R.
supporting information; experimental part, p. 6309 - 6314 (2011/08/07)
Two is better than one: We demonstrate the viability of an organocatalytic reaction sequence along a short peptide backbone that carries two independent catalytic functionalities, which allow the rapid, one-pot acylative desymmetrization and oxidation of meso-alkane-1,2-diols to the corresponding acetylated acetoins with good yields and enantioselectivities (see scheme). Copyright
Aerobic oxidation of alkenes to esters of vicinal diols with a syn-configuration catalyzed by I2 and the H5PV 2Mo10O40 polyoxometalate
Branytska, Olena,Neumann, Ronny
, p. 2525 - 2527 (2007/10/03)
A new method for the synthesis of vicinal diols from alkenes has been developed. Reaction of molecular iodine in the presence of a polyoxometalate as oxidation catalyst under aerobic conditions in acetic acid solvent leads to the oxidative iodoacetoxylation of an alkene, i.e. formation of a 1,2-iodoacetate. Further in situ substitution of the iodide by water yields the 1,2-diol monoacetate with a predominantly (ca. 4.5:1) cis-configuration. Further esterification under the reaction's acidic conditions leads also to the cis-diacetate. The method may be valuable for the synthesis of cis-vicinal diols without use of toxic osmium catalysts. Georg Thieme Verlag Stuttgart.
Adrenaline profiling of lipases and esterases with 1,2-diol and carbohydrate acetates
Wahler, Denis,Boujard, Olivier,Lefèvre, Fabrice,Reymond, Jean-Louis
, p. 703 - 710 (2007/10/03)
The adrenaline test for enzymes is a general back-titration procedure to detect 1,2-diols, 1,2-aminoalcohols and α-hydroxyketones reaction products of enzyme catalysis by colorimetry. The method was used to profile a series of esterases and lipases for their esterolytic activity on a series of carbohydrate and polyol acetates. Substrates were prepared by peracetylation and used for parallel microtiter-plate analysis of enzyme activities. This method can be used to achieve a rapid and automated characterization of a set of enzymes during HTS screening.
A one-step procedure for the monoacylation of symmetrical 1,2-diols
Clarke, Paul A.,Kayaleh, Nadim E.,Smith, Martin A.,Baker, James R.,Bird, Stephan J.,Chan, Chuen
, p. 5226 - 5231 (2007/10/03)
A series of lanthanide (III) salts have been shown to catalyze the monoacylation of symmetrical 1,2-diols by carboxylic acid anhydrides with surprisingly high selectivity.
Rhodium(I)- and iridium(I)-catalyzed hydroboration reactions: Scope and synthetic applications
Evans, David A.,Fu, Gregory C.,Hoveyda, Amir H.
, p. 6671 - 6679 (2007/10/02)
A study of the rhodium(I)- and iridium(I)-catalyzed hydroboration of olefins with catecholborane is described. Applications to organic synthesis were one focus of this investigation. The scope of the reaction was defined, and issues of stereoselection were addressed. The rhodium-catalyzed hydroboration of several classes of allylic alcohols was found to be highly diastereoselective, preferentially affording the isomer complementary to that furnished by the uncatalyzed variant of the reaction (9-BBN). The first two general approaches to effecting a directed olefin hydroboration were developed. Both phosphinites and amides proved capable of delivering the transition metal reagent.
The Use of Bismuth(III) Acetate in 'Wet' and 'Dry' Prevost Reactions
Trainor, Robert W.,Deacon, Glen B.,Jackson, W. Roy,Giunta, Nunzio
, p. 1265 - 1280 (2007/10/02)
cis-Diol and trans-diol derivatives can be prepared from alkenes by reaction with iodine and bismuth(III) acetate in 'wet' and 'dry' acetic acid, respectively.Reactions using lesser amounts of bismuth(III) acetate under 'dry' conditions give iodo acetates and under 'wet' conditions a mixture of iodohydrins and iodo ethers.Comparison of these reactions with those promoted by silver, copper, mercury and thallium salts is included.
Bismuth(III) Acetate: A Cheap, Efficient, and Environmentally Acceptable Reagent for 'Wet' and 'Dry' Prevost Reactions
Campi, Eva M.,Deacon, Glen B.,Edwards, Gavin L.,Fitzroy, Mark D.,Giunta, Nunzio,et al.
, p. 407 - 408 (2007/10/02)
cis- and trans-Diol derivatives can be prepared from alkenes by reaction with bismuth(III) acetate in 'wet' and 'dry' acetic acid respectively.
COORDINATION AND CATALYTIC REACTIONS OF UNSATURATED COMPOUNDS. VIII. HETEROGENEOUS CATALYTIC ACETOXYLATION OF 1-HEXENE AND CYCLOHEXENE
Devekki, A. V.,Yakushkin, M. I.,Egor'kov, A. N.,Belyaeva, N. V.,Mozzhukhina, T. N.,et al.
, p. 1680 - 1684 (2007/10/02)
During the acetoxylation of 1-hexene and cyclohexene in acetic acid in the presence of atmospheric oxygen and intermetallic compounds based on palladium and rhodium the ester groups are introduced into the substrate molecule.In the case of 1-hexene, the monoacetates of 1,2-hexanediol and 3-acetoxy-1-hexene are formed preferentially.The reactivity of the cyclic alkene is more clearly defined than that of the acyclic analog, and the catalyzate contains the cis- and trans-diacetoxy derivatives, 3-acetoxycyclohexene, and the products from ring concentration.The difference in the catalytic activity of the palladium and rhodium intermetallic compounds shows up mainly in the actoxylation of 1-hexene.The ring concentration products are evidently formed in the stages involving the transformation of the actoxonium ion.
