14467-53-9Relevant academic research and scientific papers
Efficient Synthesis of 2-Amino-1-Arylethanols Through a Lewis Base-Catalyzed SiCl4-Mediated Asymmetric Passerini-Type Reaction
Ayad, Tahar,Gernet, Aurélie,Pirat, Jean-Luc,Ratovelomanana-Vidal, Virginie,Virieux, David
supporting information, p. 6497 - 6500 (2020/10/30)
We herein report, a practical and efficient strategy for the synthesis of enantiomerically enriched 2-amino-1-arylethanols, a structural motif commonly encountered in the family of β-adrenergic blockers or agonists, through a Lewis base-catalyzed SiClsub
Efficient one-pot synthesis of unsymmetrical gold(I) N-heterocyclic carbene complexes and their use as catalysts
Hashmi, A. Stephen K.,Yu, Yang,Rominger, Frank
experimental part, p. 895 - 904 (2012/04/04)
Eleven different gold(I) complexes of new NHC ligands were prepared in excellent yield, demonstrating the versatility of the new route to NHC complexes. While the influence of electronically different ligands on the synthesis of the catalysts was small, the catalytic activities of the products differed significantly.
2-Aryl-2-hydroxyethylamine substituted 4-oxo-4,7-dihydrothieno[2,3-b]pyridines as broad-spectrum inhibitors of human herpesvirus polymerases
Schnute, Mark E.,Anderson, David J.,Brideau, Roger J.,Ciske, Fred L.,Collier, Sarah A.,Cudahy, Michele M.,Eggen, MariJean,Genin, Michael J.,Hopkins, Todd A.,Judge, Thomas M.,Kim, Euibong J.,Knechtel, Mary L.,Nair, Sajiv K.,Nieman, James A.,Oien, Nancee L.,Scott, Allen,Tanis, Steven P.,Vaillancourt, Valerie A.,Wathen, Michael W.,Wieber, Janet L.
, p. 3349 - 3353 (2008/02/07)
A novel series of 2-aryl-2-hydroxyethylamine substituted 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamides have been identified as potent antivirals against human herpesviruses. These compounds demonstrate broad-spectrum inhibition of the herpesvirus polymerases HCMV, HSV-1, EBV, and VZV with high specificity compared to human DNA polymerases.
The direct catalytic asymmetric α-aminooxylation reaction: Development of stereoselective routes to 1,2-diols and 1,2-amino alcohols and density functional calculations
Cordova, Armando,Sunden, Henrik,Bogevig, Anders,Johansson, Mikael,Himo, Fahmi
, p. 3673 - 3684 (2007/10/03)
Proline-catalyzed direct asymmetric α-aminooxylation of ketones and aldehydes is described. The proline-catalyzed reactions between unmodified ketones or aldehydes and nitrosobenzene proceeded with excellent diastereo- and enantioselectivities. In all cases tested, the corresponding products were isolated with > 95% ees. Methyl alkyl ketones were regiospecifically oxidized at the methylene carbon atom to afford enantiomerically pure α-aminooxylated ketones. In addition, cyclic ketones could be α,α′-dioxidized with remarkably high selectivity, furnishing the corresponding diaminooxylated ketones with > 99% ees. The reaction mechanism of the proline-catalyzed direct asymmetric α-aminooxylation was investigated, and we performed density functional theory (DFT) calculations in order to investigate the nature of the plausible transition states further. We also screened other organocatalysts for the asymmetric α-oxidation reaction and found that several proline derivatives were also able to catalyze the transformation with excellent enantioselectivities. Moreover, stereoselective routes for the synthesis of monoprotected vicinal diols and hydroxyketones were found. In addition, short routes for the direct preparation of enantiomerically pure epoxides and 1,2-amino alcohols are presented. The direct catalytic α-oxidation is also a novel route for the stereoselective preparation of β-adrenoreceptor antagonists.
Preparation of phenolic chiral crown ethers and podands and their enantiomer recognition ability toward secondary amines
Hirose, Keiji,Fujiwara, Akihito,Matsunaga, Kazuhisa,Aoki, Nobuaki,Tobe, Yoshito
, p. 555 - 566 (2007/10/03)
Phenolic pseudo-24-crown-8 (S,S)-3, pseudo-27-crown-9 (S,S)-4, and podands (R,R)-5 and (R,R)-6 possessing phenyl groups as chiral barriers were prepared and their chiral recognition properties toward secondary neutral amines were examined. Pseudo-24-crown-8 (S,S)-3 and podand (R,R)-5 showed sufficient binding ability and moderate chiral recognition ability toward secondary amines.
Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: Application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes
Saravanan,Bisai, Alakesh,Baktharaman,Chandrasekhar,Singh, Vinod K
, p. 4693 - 4706 (2007/10/03)
A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides. The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product.
Asymmetric Reduction of α-Ketoimines with Oxazaborolidine Catalysts: A Novel, Practical Approach to Chiral Arylethanolamines
Hong, Yaping,Gao, Yun,Nie, Xiaoyi,Zepp, Charles M.
, p. 5551 - 5554 (2007/10/02)
Asymmetric borane reduction of α-ketoimines with oxazaborolidine catalysts has been studied.The ee's of the resulting arylethanolamines are uo to 93percent using 20 molpercent of the catalyst.
Boranes in Synthesis. 6. A New Synthesis of β-Amino Alcohols from Epoxides. Use of Lithium Amides and Aminoborane Catalysts To Synthesize β-Amino Alcohols from Terminal and Internal Epoxides in High Yield
Harris, Clifford E.,Fisher, Gary B.,Beardsley, David,Lee, Lawrence,Goralski, Christian T.,et al.
, p. 7746 - 7751 (2007/10/02)
A study of the conversion of terminal and internal epoxides to the corresponding β-amino alcohols using simple primary and secondary lithium amides has been carried out.Thus, styrene oxide and 1,2-epoxydodecane react directly with primary and secondary lithium amides in THF at 25 deg C to give a single regioisomer of the corresponding β-amino alcohols in 80-100percent isolated yields.Since internal epoxides are known to yield predominantly allylic alcohols when reacted with lithium amides, we employed a series of aminoborane Lewis-acid catalists, generated in situ, to suppress formation of the allylic alcohols.Thus, the reaction of cyclohexene oxide with a variety of primary and secondary lithium amides at 34 deg C in diethyl ether in the presence of a catalytic amount of B-bromo-9-BBN afforded the corresponding β-amino alcohols in 70-95percent isolated yield.
Asymmetric syntheses with a new optically active perhydronaphthalene based chiral auxiliary
Hamon,Holman,Massy-Westropp
, p. 9593 - 9604 (2007/10/02)
(1R,4aS,8S,8aS)-8-(5'-Methoxy-2'-methylphenyl)-8-methyldecahydro-1-nap hthalenol 3a is a highly efficient chiral auxiliary in the Diels-Alder addition of its acrylate ester 5 and in the DIBAL-H and Grignard reactions of its phenylglyoxylate ester 7.
Inexpensive Reagents for the Synthesis of Amides from Esters and for Regioselective Opening of Epoxides
Solladie-Cavallo, A.,Bencheqroun, M.
, p. 5831 - 5834 (2007/10/02)
Lithium aluminum amides , 6a-6d, easily prepared in Et2O or THF from 1 equiv of LiAlH4 and 5 equiv of amine, proved to be efficient reagents for the synthesis of secondary amides from esters (ca. 100 percent with unhindered amines and 92 percent with t-BuNH2).They also open aryl epoxides with very high regioselectivity to give 97-98 percent of the β-amino-α-arylethanols (corresponding to the SN2 mechanism).
