- Visible-light-mediated three-component Minisci reaction for heteroarylethyl alcohols synthesis
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Methods for heteroarylethyl alcohol synthesis are critical to the chemical and pharmaceutical industries. Herein, we report a mild, modular, practical Minisci reaction for catalytic synthesis of heteroarylethyl alcohols via sequential addition of H2O and N-heteroarenes across olefinic double bonds. This scalable protocol was used for direct hydroxy-heteroarylation of olefins with a wide range of N-heteroarenes and can be expected to permit rapid conversion of abundant feedstock materials into medically relevant molecules.
- Dong, Jianyang,Liu, Jianhua,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin,Yue, Fuyang
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supporting information
p. 7963 - 7968
(2021/11/01)
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- Improved synthesis of cyclohexane-backbone iridium-complexes of quinoline-phosphine and their applications in asymmetric hydrogenation
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– The iridium-complexes 3 and 4 with cyclohexane-backbone derived from quinoline were easily synthesized. The key step is cis/trans stereoselective reduction of 2-(quinolin-2-yl)cyclohexanone 5 to trans-2-(quinolin-2-yl)cyclohexanol 6 using Al(Oi-Pr)3/i-P
- Liu, Qibin
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- Synthesis of chiral P,N-ligands derived from quinoline and their application in asymmetric allylic alkylations
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Chiral P,N-ligands derived from quinoline and with a trans and cis cyclohexane backbone were easily synthesised in four steps from quinoline N-oxide. The enantiopure trans isomer was obtained by the way of chiral resolution of the mixture of trans- and cis-2-(quinolin-2-yl)cyclohexanol with dibenzoyltartaric acid and then subjected to a Mitsunobu reaction and deprotection to give the corresponding cis isomer. The optical pure trans and cis isomer reacted with chlorodiphenylphosphine or PAr2NEt 2 to obtain trans and cis P,N-ligands, which were used in asymmetric allylic alkylations with up to 78% ee and 84% ee respectively.
- Shen, Yan-Hong,Lv, Hui-Chao,Zhao, Liang
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scheme or table
p. 349 - 351
(2011/10/05)
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- 1H NMR determination of absolute configuration of 1- or 2-aryl-substituted alcohols and amines by means of their diastereomers: Novel separation technique of diastereomeric derivatives of pyridyl alcohols by extraction
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Abstract: A convenient method to determine the absolute configuration of trans-2-aryl cyclohexanols, 1-aryl alcohols and amines was achieved. This method takes advantage of the 1H NMR spectroscopic observations of the remarkable high-field shift of C18-CH3 protons caused by the aromatic shielding effect. It is based on a discrimination of the difference of the environments in two diastereomers derived from 3β-acetoxy-5-etienic acid. Furthermore, it was observed that the corresponding diastereomeric derivatives of the pyridyl alcohols were simply separated by extraction based on the difference in their basicity.
- Matsugi, Masato,Itoh, Kinuyo,Nojima, Masatomo,Hagimoto, Yuri,Kita, Yasuyuki
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p. 5551 - 5564
(2007/10/03)
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- Electron-transfer Processes: Metal Salt Catalysed Oxidation of Olefins by Peroxydisulphate
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The reaction of simple olefins (oct-1-ene, oct-2-ene, cyclohexene, cycloheptene) with peroxydisulphate has been investigated under several conditions: (i) in aqueous medium and catalysis by AgI, FeII, and CuII; (ii) in acetic madium and catalysis by CuII, FeIII; (iii) in the presence of traps of nucleophilic alkyl radicals (protonated heteroaromatic bases and 1,4-benzoquinone either in water or in acetic acid).The catalyst and the radical trap govern the selectivity and allow a variety of new synthetic achievements.Evidence for a unified initial mechanism of electron transfer with formation of a radical cation from the olefin is reported to explain all the results.In water the radical cation gives a β-hydroxyalkyl radical, which, depending on the nature of the catalyst and the trap, can give the corresponding saturated alcohol by hydrogen abstraction, the products of CuII oxidation, or β-hydroxyalkylation of the heteroaromatic compound or 1,4-benzoquinone.In acetic acid the radical cation gives a β-acetoxyalkyl radical, which is oxidized to the corresponding allylic acetate by copper(II) acetate or trapped by the heteroaromatic base.
- Arnoldi, Claudio,Citterio, Attilio,Minisci, Francesco
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p. 531 - 542
(2007/10/02)
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