Asymmetric iodoamination of chalcones and 4-aryl-4-oxobutenoates catalyzed by a complex based on scandium(III) and a N,N′-dioxide ligand

Cai Y.; Liu X.; Li J.; Chen W.; Wang W.; Lin L.; Feng X.

首页> 外文期刊>Chemistry: A European journal >Asymmetric iodoamination of chalcones and 4-aryl-4-oxobutenoates catalyzed by a complex based on scandium(III) and a N,N′-dioxide ligand

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Asymmetric iodoamination of chalcones and 4-aryl-4-oxobutenoates catalyzed by a complex based on scandium(III) and a N,N′-dioxide ligand

机译：scan（III）和N，N'-二氧化物配体的配合物催化查尔酮和4-芳基-4-氧代丁烯酸酯的不对称碘胺化

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Highly diastereo- and enantioselective iodoamination of chalcones, 4-aryl-4-oxobutenoates, and a trifluoro-substituted enone has been accomplished in the presence of a chiral N,N′-dioxide/[Sc(OTf) _3] complex (0.5-2 mol%), delivering the desired vicinal anti-α-iodo-β-amino carbonyl compounds regioselectively in high yields (up to 97%) and with excellent diastereoselectivities (>99:1 d.r.) and enantioselectivities (up to 99% ee). Enantiopure syn-α-iodo-β-amino products could also be obtained from the isomerization of particular iodo compounds. TsNHX species (X=Cl, Br, I), generated from the reactions between the halo sources and TsNH _2, were further confirmed as the active species in the haloamination reactions involved in the formation of the key halonium ion intermediates. A typical haloamination dependency was observed, with reactivity decreasing in the order NBS>NIS?NCS.

机译：查尔酮，4-芳基-4-氧代丁烯酸酯和三氟取代的烯酮的高度非对映和对映选择性碘化已在手性N，N'-二氧化物/ [Sc（OTf）_3]络合物（0.5- 2 mol％），以高产率（高达97％）区域选择性地提供所需的邻位抗α-碘-β-氨基羰基化合物，并具有出色的非对映选择性（> 99：1 dr）和对映选择性（高达99％ee）。对映体纯的α-碘-β-氨基产物也可以通过特定碘化合物的异构化获得。由卤素源和TsNH _2之间的反应生成的TsNHX物种（X = Cl，Br，I）被进一步确认为参与关键的ion离子中间体形成的卤化反应中的活性物种。观察到典型的卤化依赖性，反应性以NBS> NIS→NCS的顺序降低。

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《Chemistry: A European journal》 |2011年第52期|共6页
作者
Cai Y.; Liu X.; Li J.; Chen W.; Wang W.; Lin L.; Feng X.;
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正文语种 eng
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关键词
asymmetric catalysis; dioxides; iodoamination; iodonium ions; scandium;

机译：不对称催化;二氧化物;碘胺化;碘离子;scan;

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1. Asymmetric Iodoamination of Chalcones and 4-Aryl-4-oxobutenoates Catalyzed by a Complex Based on Scandium(III) and a N,N′-Dioxide Ligand [J] . Yunfei Cai Prof. Dr., Xiaohua Liu, Jun Li, Chemistry - A European Journal . 2011,第52期

机译：Scan（III）和N，N'-二氧化物配体的配合物催化的查尔酮类和4-芳基-4-氧代丁烯酸酯的不对称碘胺化
2. Asymmetric ring-opening of cyclopropyl ketones with beta-naphthols catalyzed by a chiral N,N '-dioxide-scandium(III) complex [J] . Xia Yong, Chang Fenzhen, Lin Lili, Organic Chemistry Frontiers . 2018,第8期

机译：与β-萘酚的环丙基酮的不对称开环，催化由手感N，N'二氧化物 - 钪（III）复合物催化
3. Highly Efficient Asymmetric Synthesis of Chiral gamma-Alkenyl Butenolides Catalyzed by Chiral N,N '-Dioxide-Scandium(III) Complexes [J] . Ji Jie, Lin Lili, Tang Qiong, ACS catalysis . 2017,第6期

机译：高效的不对称合成由手感催化的手性γ-链烯基丁烯醇胺催化，N，N'-二氧化钪 - 钪（III）络合物催化
4. Asymmetric Oxindole Synthesis Catalyzed by Palladium Complexes with Unsymmetrical Chiral Bioxazoline-Based Carbene Ligands [C] . Daisuke Imao, Naruhito Ebata, Yuki Yamaguchi Symposium on Organometallic Chemistry . 2006

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5. Asymmetric Friedel-Crafts alkylations catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes. [D] . Fandrick, Keith Richard. 2007

机译：双（恶唑啉基）吡啶-三氟甲磺酸scan（III）催化的不对称Friedel-Crafts烷基化反应。
6. Formation and ligand-based reductive chemistry of bridged bis-alkylidene scandium(iii) complexes [O] . Wangyang Ma, Chao Yu, Yue Chi, 2018

机译：桥联双亚烷基scan（iii）配合物的形成和基于配体的还原化学
7. N,N′-Dioxide–Scandium(III)-Catalyzed Asymmetric Michael Addition [O] . 2013

机译：n，n'二氧化钪 - 钪（iii） - 催化不对称迈克尔加法

Asymmetric iodoamination of chalcones and 4-aryl-4-oxobutenoates catalyzed by a complex based on scandium(III) and a N,N′-dioxide ligand

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