65469-88-7Relevant articles and documents
Long-chain syn-1-phenylalkane-1,3-diyl diacetates, related phenylalkane derivatives, and sec-alcohols, all possessing dominantly iso-branched chain termini, and 2/3-methyl-branched fatty acids from Primula veris L. (Primulaceae) wax
Radulovi?, Niko S.,?ivkovi? Sto?i?, Milena Z.
, (2021)
Herein, the results of the first study of non-flavonoid constituents of aboveground surface-wax washings of Primula veris L. (Primulaceae) are presented. Chromatography of the washings yielded a minor fraction composed of n-, iso-, and anteiso-series of l
Proline-functionalized metal-organic frameworks and their use in asymmetric catalysis: Pitfalls in the MOFs rush
Canivet, Jerome,Farrusseng, David
, p. 11254 - 11256 (2015)
Post-functionalisation of metal-organic frameworks is a very efficient and elegant method for designing tailor-made chiral solids for selective asymmetric catalysis. However, erroneous data and misinterpretation can easily occur. We report some best pract
Photocatalysis with Quantum Dots and Visible Light: Selective and Efficient Oxidation of Alcohols to Carbonyl Compounds through a Radical Relay Process in Water
Zhao, Lei-Min,Meng, Qing-Yuan,Fan, Xiang-Bing,Ye, Chen,Li, Xu-Bing,Chen, Bin,Ramamurthy, Vaidhyanathan,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 3020 - 3024 (2017/03/13)
Selective oxidation of alcohols to aldehydes/ketones has been achieved with the help of 3-mercaptopropionic acid (MPA)-capped CdSe quantum dot (MPA-CdSe QD) and visible light. Visible-light-prompted electron-transfer reaction initiates the oxidation. The thiyl radical generated from the thiolate anion adsorbed on a CdSe QD plays a key role by abstracting the hydrogen atom from the C?H bond of the alcohol (R1CH(OH)R2). The reaction shows high efficiency, good functional group tolerance, and high site-selectivity in polyhydroxy compounds. The generality and selectivity reported here offer a new opportunity for further applications of QDs in organic transformations.
Catalytic 1,3-difunctionalisation of organic backbones through a highly stereoselective, one-pot, boron conjugate-addition/reduction/oxidation process
Sole, Cristina,Tatla, Amolak,Mata, Jose A.,Whiting, Andrew,Gulyas, Henrik,Fernandez, Elena
supporting information; experimental part, p. 14248 - 14257 (2012/01/19)
A simple one-pot, three-step synthetic route to chiral 1,3-amino alcohols and 1,3-diols has been established. Considering the overall stereocontrol of the synthetic protocol, the first and key step is an enantioselective β-boration of α,β-unsaturated imin
C-O hydrogenolysis catalyzed by Pd-PMHS nanoparticles in the company of chloroarenes
Rahaim, Ronald J.,Maleczka, Robert E.
supporting information; experimental part, p. 584 - 587 (2011/04/23)
Catalytic Pd(OAc)2 and polymethylhydrosiloxane (PMHS), in conjunction with aqueous KF, and a catalytic amount of an aromatic chloride, effects the chemo-, regio-, and stereoselective deoxygenation of benzylic oxygenated substrates at room temperature in THF. Preliminary mechanistic experiments suggest the process to involve palladium-nanoparticle-catalyzed hydrosilylation followed by C-O reduction. The chloroarene additive appears to facilitate the hydrogenolysis process through the slow controlled release of HCl.
1,3-Diol synthesis via controlled, radical-mediated C-H functionalization
Chen, Ke,Richter, Jeremy M.,Baran, Phil S.
, p. 7247 - 7249 (2008/12/21)
The invention of a method for the synthesis of 1,3-diols from the corresponding alcohols is described, via controlled, radical-mediated C-H functionalization. The sequence described herein entails near quantitative conversion to the corresponding trifluoroethyl carbamate, followed by a variant of the Hofmann-Loffler-Freytag reaction, cyclization, and hydrolysis to provide the 1,3-diols. In addition to the 10 examples presented herein, the syntheses of four natural products are facilitated by this directed oxyfunctionalization. This methodology is demonstrated to be orthogonal to other known C-H oxidations. Finally, this sequence is efficient, practical, inexpensive, and scalable. Copyright
Facile deoxygenation of dicarbonyl compounds using a samarium diiodide-additive system
Kamochi, Yasuko,Kudo, Tadahiro,Masuda, Toshinobu,Takadate, Akira
, p. 1017 - 1020 (2007/10/03)
The reduction of α- and β-dicarbonyl compounds was investigated with samarium diiodide in the presence of additive. Diketones and ketocarboxylic acids were easily reduced at room temperature to give the mono-alcohols in good to excellent yield, and ketoester afforded the saturated ester as the major product in moderate yield. These reductions containing the reductive deoxygenation can be rapidly performed under the facile and mild conditions by this method.
Diastereomer-differentiating hydrolysis of 1,3-diol-acetonides: A simplified procedure for the separation of syn-and anti-1,3-diols
Bode, Silke E.,Muller, Michael,Wolberg, Michael
, p. 619 - 621 (2007/10/03)
(formula presented) A new method to facilitate the separation of diastereomeric syn- and anti-1,3-diols is described. The method relies on the different hydrolysis rates of the corresponding diastereomeric acetonides. Treatment of a dichloromethane solution of syn- and anti-1,3-diol-acetonide with a catalytic amount of diluted aqueous hydrochloric acid leads to the selective cleavage of the anti diastereomer. The resulting anti-1,3-diol can be easily separated from the unchanged syn-1,3-diol-acetonide.
Stereoselective radical aryl migration from silicon to carbon
Amrein, Stephan,Bossart, Martin,Vasella, Tomaso,Studer, Armido
, p. 4281 - 4288 (2007/10/03)
Highly diastereoselective radical 1,5 phenyl migration reactions from silicon in diarylsilyl ethers to various C-centered radicals to form the corresponding 3-phenylated alcohols are described. Functionalized aryl groups can also be transferred. The effect of the variation of the attacking radical on the aryl transfer reaction is discussed. Best results are obtained for the phenyl migration to nucleophilic secondary alkyl radicals, where high yields (up to 81%) and high selectivities (up to 95% ds) have been obtained. The mechanism of the process is discussed and a model to explain the stereochemical outcome of the reaction is presented. Finally, stereoselective 1,4 aryl migration reactions from Si to C, including a new method for the α- arylation of esters, are presented.
