24112-80-9Relevant academic research and scientific papers
Lipase-catalyzed regioselective monoacetylation of unsymmetrical 1,5-primary diols
Oger, Camille,Marton, Zsuzsanna,Brinkmann, Yasmin,Burtel-Ponce, Valerie,Durand, Thierry,Graber, Marianne,Galano, Jean-Marie
supporting information; experimental part, p. 1892 - 1897 (2010/05/19)
"Chemical Equation Presented" Lipase B from Candida antarctica (CALB) has been selected as the most suitable enzyme to catalyze the regioselective monoacetylation of 1,5-diol isoprostane intermediate, using vinyl acetate as an acyl transfer reagent in TIIF. We next applied this reaction on linear 2-substituted, 2,2′-disubstituted-l,5pentanediols, and, cyclic 2,3-disubstituted-l,5-pentanediols. To rationalize the regioselectivity observed, molecular docking simulations were performed.
The Stereochemistry of Organometallic Compounds. XXXVIII. Regio- and Stereo-control in the Rhodium-Catalysed Hydroformylation of Some Alkenyl Phosphites
Jackson, W. Roy,Moffat, Mark R.,Perlmutter, Patrick,Tasdelen, E. Elizabeth
, p. 823 - 834 (2007/10/02)
Excellent regiocontrol is achieved in the rhodium-catalysed hydroformylation of some alkenyl phosphites, and good stereocontrol is obtained in the hydroformylation of some cyclohexenyl phosphites.The stereochemical results have implications for the mechanism of these rhodium-catalysed reactions.
Intermolecular Stereoselective Pummerer Reactions of 4-(p-Chlorophenyl)thiane 1-Oxides and trans-1-Thiadecalin 1-Oxides and 2-Thiadecalin 2-Oxides with Acetic Anhydride
Oae, Shigeru,Itoh, Osamu,Numata, Tatsuo,Yoshimura, Toshiaki
, p. 270 - 279 (2007/10/02)
The Pummerer reactions of cnformationally fixed 4-(p-chlorophenyl)thiane 1-oxides and trans-1-thiadecalin 1-oxides and trans-2-thiadecalin 2-oxides with acetic anhydride are either stereoselective or stereospecific, both in the absence and in the presence of a scavenger of acetic acid formed, such as dicyclohexylcarbodiimide (DCC) or 2,6-lutidine.However, the 18O-tracer experiments with the 18O-labeled sulfoxide revealed the reaction to be an intermolecular rearrangement, while the kinetic experiment with α-deuterated 4-(p-chlorophenyl)thiane 1-oxides gave sizable values of kinetic isotope effect, i.e., 2.8 for the cis isomer and 3.4 for the trans isomer.In the reaction of 4-arylthiane 1-oxides with acetic anhydride, the thermodynamically controlled product is axial 2-acetoxy-4-(p-chlorophenyl)thiane while the kinetically controlled product is the equatorial isomer which is formed in the presence of the acid scavenger, DCC.In the Pummerer reaction of the thiadecalins S-oxides the equatorial α-acetoxy sulfides are the preferential products, however, the isomer preference is more pronounced in the reaction with DCC.These observations, along with other pertinent data seem to suggest that the rate-determining step in the Pummerer reaction of these simple heterocyclic sulfoxides is E2 elimination of acetic acid from the acetoxysulfonium intermediates.
Models for Glycoside Hydrolysis. Synthesis and Hydrolytic Studies of the Anomers of a Conformationally Rigid Acetal
Eikeren, Paul van
, p. 4641 - 4645 (2007/10/02)
The methyl acetals of 2-hydroxy-3-oxa-trans-decalin were synthesized as models for conformationally rigid methyl glycosides.The compounds were prepared by Baeyer-Villiger oxidation of trans-hexahydrohydrindan-2-one followed by reduction of the resulting lactone with diisobutylaluminum hydride.Treatment of the hemiacetal with methanol and an acid catalyst afforded a mixture of acetals which were separated by chromatography and identified by NMR.Hydrolytic studies were carried out under a range of acid concentrations and temperatures.The mechanistic implications of the relative hydrolysis rates (axial/equatorial ratio of 1.51+/-0.22) and activation parameters are discussed.
