- Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2
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A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.
- Hu, Le' an,Zhang, Yao,Zhang, Qing-Wen,Yin, Qin,Zhang, Xumu
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supporting information
p. 5321 - 5325
(2020/02/28)
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- Direct enantioseparation of 1-(2-hydroxyphenyl) ethylamines via diastereomeric salt formation: Chiral recognition mechanism based on the crystal structure
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In this study, the direct enantioseparation of unprotected 1-(2-hydroxyphenyl)ethylamines (1a and 1b) via diastereomeric salt formation is reported. After the one-pot synthesis of racemic 1, the screening of seven acidic chiral resolving agents showed tha
- Kodama, Koichi,Hayashi, Naoki,Fujita, Mikidai,Hirose, Takuji
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p. 25609 - 25615
(2014/07/07)
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- Design and synthesis of chiral oxathiozinone scaffolds: Efficient synthesis of hindered enantiopure sulfinamides and sulfinyl ketimines
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Is that S-O? The title scaffolds have a highly active and properly differentiated S-O bond for the efficient synthesis of enantiopure sulfinamides. The method is practical, green, and has the potential to provide an economical commercial process for the synthesis of bulky sulfinamides. Copyright
- Han, Zhengxu S.,Herbage, Melissa A.,Mangunuru, Hari P. R.,Xu, Yibo,Zhang, Li,Reeves, Jonathan T.,Sieber, Joshua D.,Li, Zhibin,Decroos, Philomen,Zhang, Yongda,Li, Guisheng,Li, Ning,Ma, Shengli,Grinberg, Nelu,Wang, Xiaojun,Goyal, Navneet,Krishnamurthy, Dhileep,Lu, Bruce,Song, Jinhua J.,Wang, Guijun,Senanayake, Chris H.
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supporting information
p. 6713 - 6717
(2013/07/26)
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- Chiral phosphoric acid-catalyzed enantioselective transfer hydrogenation of ortho-hydroxyaryl alkyl N - H ketimines
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The first enantioselective chiral phosphoric acid-catalyzed transfer hydrogenation of unprotected ortho-hydroxyaryl alkyl N - H ketimines using Hantszch di-tert-butyl ester as a reductant is reported. A variety of ortho-hydroxybenzylamines were obtained in good to excellent yields and enantiomeric excesses.
- Nguyen, Thanh Binh,Bousserouel, Hadjira,Wang, Qian,Gueritte, Francoise
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supporting information; experimental part
p. 4705 - 4707
(2010/12/24)
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- Enantioselective synthesis of primary 1-(aryl)alkylamines by nucleophilic 1,2-addition of organolithium reagents to hydroxyoxime ethers and application to asymmetric synthesis of G-protein-coupled receptor ligands
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(E)-Arylaldehyde oxime ethers bearing a (1S)-2-hydroxy-1-phenylethyl or (2R)-1-hydroxy-2-phenylethyl group as a chiral auxiliary, both derived from a single precursor, methyl (R)-mandelate, underwent nucleophilic addition with organolithium reagents via six-membered chelates to give the diastereomerically enriched (R)- and (S)-adducts, respectively, which, after chiral auxiliary removal by reductive N-O bond cleavage, led to the corresponding (R)- and (S)-1-(aryl)ethylamines. This organolithium addition protocol using methyllithium was applied in an enantiodivergent fashion to the preparation of both enantiomers of 1-(2-hydroxyphenyl)ethylamine, which has been previously used as an efficient chiral auxiliary for the synthesis of natural products in this laboratory. The synthetic utility of this methodology involving diastereoselective methyl addition was demonstrated by further application to the asymmetric synthesis of a new type of calcium receptor agonist (calcimimetics), (R)-(+)-NPS R-568 and its thio analogue. Furthermore, diastereoselective vinylation was accomplished by application of the hydroxy oxime ether-based protocol using vinyllithium, which allowed the development of the enantioselective synthesis of the NK-1 receptor antagonists, (+)-CP-99,994 and (+)-CP-122,721.
- Atobe, Masakazu,Yamazaki, Naoki,Kibayashi, Chihiro
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p. 5595 - 5607
(2007/10/03)
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