- Directed Nickel-Catalyzed Diastereoselective Reductive Difunctionalization of Alkenyl Amines
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We report herein an intermolecular syn-arylalkylation and alkenylalkylation of alkenyl amines with two different organohalides (iodides and bromides) using Ni(II) catalyst. The cleavable bidentate quinolinamide is utilized after extensive directing group screening to enable olefin difunctionalization with high levels of regio-, chemo-, and diastereocontrol. This general and practical protocol is compatible with α- or β-substituted terminal alkenes and internal alkenes, providing rapid access to branched aliphatic amines bearing two skipped and vicinal stereocenters with high diastereoselectivities that would otherwise be difficult to synthesize.
- Zhao, Lei,Meng, Xiao,Zou, Yifeng,Zhao, Junsong,Wang, Lili,Zhang, Lanlan,Wang, Chao
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p. 8516 - 8521
(2021/10/25)
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- Palladium-catalyzed direct arylation of allylamines with simple arenes
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The Pd(OAc)2-catalyzed direct C-H bond olefination of unreactive arenes with allylamines in the presence of AgOAc was developed. A variety of allylamines including β-substituted substrates underwent smooth coupling reactions with various arenes
- Lei, Yichao,Qiu, Ruiying,Zhang, Lingjuan,Xu, Conghui,Pan, Yixiao,Qin, Xubo,Li, Huanrong,Xu, Lijin,Deng, Yuheng
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p. 1275 - 1279
(2015/04/27)
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- Synthesis and pharmacological characterization of novel 6-fluorochroman derivatives as potential 5-HT(1A) receptor antagonists
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A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT(1A) receptor. N-2-[[(6-Fluorochroman-8- yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252- 1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT(1A) receptor, some of which were selective with respect to α1-adrenergic and D2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolinstimulated adenylate cyclase assays in CHO cells expressing the human 5-HT(1A) receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screens and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3- benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT- induced behavioral and electrophysiological responses in rats.
- Yasunaga, Tomoyuki,Kimura, Takenori,Naito, Ryo,Kontani, Toru,Wanibuchi, Fumikazu,Yamashita, Hiroshi,Nomura, Tamako,Tsukamoto, Shin-Ichi,Yamaguchi, Tokio,Mase, Toshiyasu
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p. 2765 - 2778
(2007/10/03)
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- Role of the Through-Space 2p-3d Overlap Effect in the Wittig Reaction
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Reactions of the ylide derived from triphenyl(3-phthalimidopropyl)phosphonium bromide with aromatic aldehydes have been reported to give exclusively the Z alkenes.On the basis of the Bestmann mechanism for the Wittig reaction, and also because of the fact that a 2,6-dimethoxyphenyl group enters into a strong through-space 2p-3d overlap interaction with an adjacent phosphonio group, we postulated that the reactions of the ylide derived from (2,6-dimethoxyphenyl)diphenyl(3-phthalimidopropyl)phosphonium bromide with aromatic aldehydes would give substantial ratios of E:Z alkenes.This proved to be the case.
- McEwen, William E.,Cooney, John V.
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p. 983 - 987
(2007/10/02)
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