1954-91-2Relevant academic research and scientific papers
Hydroxy Group Directed Catalytic Hydrosilylation of Amides
Ni, Jizhi,Oguro, Tsubasa,Sawazaki, Taka,Sohma, Youhei,Kanai, Motomu
supporting information, p. 7371 - 7374 (2018/11/25)
Chemo- and site-selective hydrosilylation of α- or β-hydroxy amides using organocatalyst B(C6F5)3 and commercially available hydrosilanes is described. This transformation is operative under mild conditions and tolerates a wide range of functional groups. The reaction was applied for selective reduction of a specific amide group of the therapeutically important cyclic peptide cyclosporin A, demonstrating the potential usefulness of this catalytic method in late-stage structural transformations of drug lead molecules.
Synthesis and Suzuki-Miyaura cross-coupling of enantioenriched secondary potassium β-trifluoroboratoamides: Catalytic, asymmetric conjugate addition of bisboronic acid and tetrakis(dimethylamino)diboron to α,β- unsaturated carbonyl compounds
Molander, Gary A.,Wisniewski, Steven R.,Hosseini-Sarvaria, Mona
, p. 3037 - 3057 (2014/03/21)
Enantioenriched potassium β-trifluoroboratoamides have been synthesized via an asymmetric, copper-catalyzed 1,4-addition of tetrahydroxydiboron (BBA) and tetrakis(dimethylamino)-diboron to α,β-Unsaturated amides. These dibora reagents provide access to the desired organotri-fluoroborates using effective and atom economical sources of boron. The copper-catalyzed β-boration is extended to α,β- Unsaturated ketones and esters. The desired potassium organotrifluoroborates are synthesized with yields up to 92% and enantiomeric ratios up to 98:2. The enantioenriched potassium btrifluoroboratoamides are successfully cross-coupled with an array of aryl and heteroaryl chlorides in high yield with complete stereochemical fidelity as the transmetalation proceeds through an SE2 mechanism via an open transition state.
Ru-catalyzed asymmetric hydrogenation of 3-oxoglutaric acid derivatives via solvent-assisted pinpoint recognition of carbonyls in close chemical propinquity
Li, Wanfang,Ma, Xin,Fan, Weizheng,Tao, Xiaoming,Li, Xiaoming,Xie, Xiaomin,Zhang, Zhaoguo
scheme or table, p. 3876 - 3879 (2011/10/01)
Upon comparison of hydrogenation rates of various β-ketocarboxylic acid derivatives, β-ketoamides were found to be hydrogenated slightly faster than β-ketoesters in EtOH in the presence of [RuCl(benzene)(S)- SunPhos]Cl at 70 °C with 20 bar of hydrogen. In THF these differences were so sharpened that β-ketoamides were hydrogenated even faster than in EtOH while the esters were extremely slow. Based on these findings, a series of 3-oxoglutaric acid derived with ester and amide moieties on the two ends were hydrogenated to 3-hydroxyl products with high enantioselectivities.
Efficient and regioselective synthesis of 5-hydroxy-2-isoxazolines: Versatile synthons for isoxazoles, β-lactams, and γ-amino alcohols
Tang, Shibing,He, Jinmei,Sun, Yongquan,He, Liuer,She, Xuegong
supporting information; experimental part, p. 1961 - 1966 (2010/06/20)
"Chemical Equation Presented" An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy2-isoxazolines, which have been proved to be versatile synthons for isoxazles, β-hydroxy oximes, and γ-amino alcohols. β-Lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from β-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.
Chemoselective carbonyl reduction of functionalised aldehydes and ketones to alcohols with sodium dithionite
Singh, Jasvinder,Kad, Goverdhan L.,Sharma, Munisha,Dhillon
, p. 2253 - 2257 (2007/10/03)
Sodium dithionite efficiently reduces carbonyl functionalities of functionalised aldehydes and ketones to corresponding alcohols in good yields without effecting the other functional groups in water/dioxane system at 85°C.
Process for asymmetrically reducing carbonyl compounds
-
, (2008/06/13)
There is disclosed a process for asymmetrically reducing a carbonyl compound, which comprises reducing the carbonyl compound by the use of a reducing agent comprising (i) an optically active tartaric acid or ester thereof and (ii) a metal borohydride, thereby producing an optically active hydroxyl compound. The process can be used for the production of optically active hydroxyesters and alcohols from ketoesters and ketones. These products are useful for the production of medicaments and liquid crystals.
Katalytische Hydrierung und Hydrokupplung von Acetessigsaeureamiden und -estern mit dem Clusteranion - als Katalysator
Schmidt, Gerhard F.,Reiner, Josef,Suess-Fink, Georg
, p. 379 - 384 (2007/10/02)
The cluster anion - was found to catalyze the hydrogenation of the β-keto function in acetacetic amides and esters.The reaction of acetacetic amides yields the corresponding β-hydroxy derivatives, whereas acetacetic esters are converted in a consecutive coupling step into new diester derivatives.In the case of benzyl acetacetate both the hydrogenation and the hydrocoupling products were obtained.
Hydrogenolysis of the C-O Bond of the 1,2,4-Oxadiazine Ring. Adams Platinum Hydrogenation of 3-Aryl-5,6-dihydro-5-(substituted)-methylene-4H-1,2,4-oxadiazine Derivatives
Kawashima, Etsuko,Takada, Toyozo,Tabei, Katsumi
, p. 1409 - 1412 (2007/10/02)
Adams platinum hydrogenation of Z-3-aryl-5,6-dihydro-5-(substituted)methylene-4H-1,2,4-oxadiazine (1a-f) proceeds very slowly through C-O bond fission to give N-(1-substitutedcarbonyl-2-propylidene)benzamide oxime derivative 2 as the main product.In the reaction of 5-(arylcarbamoyl)methylene analogues 1d-f, 5-(arylcarbamoyl)methyl-5,6-dihydro-3-phenyl-4H-1,2,4-oxadiazine (4) and N-aryl-3-hydroxybutanamide derivative 5 are also obtained as well as compound 2.
