37886-68-3Relevant academic research and scientific papers
Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate
Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
supporting information, p. 1295 - 1298 (2019/04/13)
A novel method for the stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via the Beckmann rearrangement was developed using diphenyl phosphorazidate (DPPA) as both the oxime activator and azide source. Various ketoximes were transformed into the corresponding 1,5-disubstituted tetrazoles with exclusive trans-group migration and no E-Z isomerization of the ketoxime. This method enables the preparation of 1,5-disubstituted tetrazoles without using toxic or explosive azidation reagents.
Tandem and Selective Conversion of Tetrahydropyranyl and Silyl Ethers to Oximes Catalyzed with Trichloroisocyanuric Acid
Aghapour, Ghasem,Abbaszadeh, Zeinab
, p. 1464 - 1470 (2015/09/01)
Direct and oxidative conversion of tetrahydropyranyl and silyl ethers to oximes is described using trichloroisocyanuric acid (TCCA) as a relatively stable and inexpensive oxidant surprisingly in a catalytic amount and hydroxylamine hydrochloride under solvent-free conditions. Oximes can be synthesized from these protected alcohols in the presence of some other functional groups with excellent chemoselectivity using the present tandem catalytic method.
Chiral palladium complexes with monoterpenoids oximes
Gur'Eva,Zalevskaya,Frolova,Alekseev,Slepukhin,Kuchin
, p. 137 - 142 (2014/03/21)
Oximes of cis-caran-4-one, 3α- and 3β-hydroxycaran-4-ones, cis-verbanone, menthone, and 2β-hydroxybornan-3-one have been synthesized. The obtained oximes react with lithium tetrachloropalladate to give new chiral palladium complexes containing mono-or bid
Europium(III) triflate-catalyzed Trofimov synthesis of polyfunctionalized pyrroles
Madabhushi, Sridhar,Vangipuram, Venkata Sairam,Mallu, Kishore Kumar Reddy,Chinthala, Narsaiah,Beeram, China Ramanaiah
supporting information; body text, p. 1413 - 1416 (2012/07/13)
The synthesis of polyfunctionalized pyrroles by reaction of a ketoxime with dimethyl acetylenedicarboxylate using europium(III) triflate as the catalyst is described. Copyright
Synthesis of C 1-symmetric chiral secondary diamines and their applications in the asymmetric copper(II)-catalyzed Henry (Nitroaldol) reactions
Zhou, Yirong,Dong, Junfang,Zhang, Fanglin,Gong, Yuefa
experimental part, p. 588 - 600 (2011/03/20)
A small library of C1-symmetric chiral diamines (L1-L9) was constructed via condensing exo-(-)-bornylamine or (+)-(1S,2S,5R)-menthylamine with various Cbz-protected amino acids. Among them, ligand L1/CuCl 2?2H2O complex (2.5 mol %) shows outstanding catalytic efficiency for Henry reaction between a variety of aldehydes and nitroalkanes to afford the expected products in high yields (up to 98%) with excellent enantioselectivities (up to 99%) and moderate to good diastereoselectivities (up to 90:10). This process is air-and moisture tolerant and has been applied to the synthesis of (S)-2-amino-1-(3,4-dimethoxyphenyl) ethanol (9), a key intermediate for (S)-epinephrine and (S)-norepinephrine. On the basis of HRMS and X-ray diffraction analysis of the L1/CuCl2 complex, a transition-state model was proposed to explain the origin of asymmetric induction. The low catalyst loading, excellent yields and enantioselectivities, inexpensive copper salt, and mild reaction conditions make our catalytic system to be practically useful.
O-alkylation of menthone oxime: Synthesis and 13C NMR studies of a series of novel oxime ethers
Faisal, Saqib,Basha, Amina F.,Siddiqui, Hina,Basha, Fatima Z.
experimental part, p. 3101 - 3108 (2010/11/20)
A series of novel menthone oxime ethers were synthesized in three steps starting from (-)-menthol. Analysis of the 13C NMR chemical shift differences between carbons of oxime derivatives (O-alkyl oximes) provides a convenient and reliable means of assigning oxime stereochemistry. It has been found that carbons syn to the oxime are shifted more upfield than carbons anti to the oxime moiety. Significant E products were obtained. Copyright Taylor & Francis Group, LLC.
Synthesis and Characterization of Enantiomerically Pure Menthylamines and Their Isocyanates
Schopohl, Matthias C.,Bergander, Klaus,Kataeva, Olga,Froehlich, Roland,Waldvogel, Siegfried R.
, p. 2689 - 2694 (2007/10/03)
A synthetic protocol for optically pure (-)-menthylamine, (-)-8-methylmenthylamine, and the novel (-)-8-phenylmenthylamine is presented including a detailed characterization of these compounds and their isocyanates.
LIQUID CHROMATOGRAPHIC RESOLUTION OF RACEMIC KETONES AS THEIR OXIME 3,5-DINITROPHENYL CARBAMATES ON A CHIRAL STATIONARY PHASE
Hyun, Myung Ho,Park, Young -Whan,Baik, In-Kyu
, p. 4735 - 4738 (2007/10/02)
Cyclic and acyclic chiral ketones have been resolved as their oxime 3,5-dinitrophenyl carbamates on a chiral stationary phase derived from (S)-1-(6,7-dimethyl-1-naphthyl)isobutylamine.
C-Nitroso compounds. Part XXXVIII. Radical reactions of α-chloro-nitroso compounds with trialkylaluminium-ether complexes
Lub, J.,Beekes, M. L.,Boer, Th. J. de
, p. 161 - 167 (2007/10/02)
Ether complexes of trialkylaluminium compounds react with α-chloro-nitroso compounds via radicals which can abstract hydrogen from various solvents.In the presence of olefinic solvents, radical addition to the double bond also takes place. When the trialk
