Asymmetric Synthesis of 1,1-DiarylACHTUNGTRENUNGalkyl Units by a Copper Hydride Catalyzed Reduction: Differentiation Between Two Similar Aryl ACHTUNGTRENUNGSubstituents

Kihyun Yoo; Hyohyun Kim; Jaesook Yun

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Asymmetric Synthesis of 1,1-DiarylACHTUNGTRENUNGalkyl Units by a Copper Hydride Catalyzed Reduction: Differentiation Between Two Similar Aryl ACHTUNGTRENUNGSubstituents

机译：铜氢化物催化还原反应的不对称合成1,1-二芳基ACHTUNGTRENUNG烷基单元：两种相似的芳基乙酰基取代基之间的区别

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An efficient method for the preparation of enantiomerically enriched 1,1-diarylalkyl units has been developed. The use of copper hydride complexed by the (R)-1-[(S)-2-diphenylphosphino) ferrocenyl]ethyldicyclohexylphosphine (Josiphos) ligand effects a highly enantioselective conjugate reduction of b,b-diaryl-substituted a,b-unsaturated nitriles with aryl groups of similar steric demand and no secondary coordination site. A range of substrates with meta and para substituents on the aryl group were reduced with good to excellent enantioselectivities (up to 97% enantiomeric excess (ee)) and this methodology was applied to the formal synthesis of indatraline.

机译：已经开发了制备对映体富集的1，1-二芳基烷基单元的有效方法。与（R）-1-[（（S）-2-二苯基膦基）二茂铁基]乙基二环己基膦（Josiphos）配体络合的氢化铜的使用可实现b，b-二芳基取代的a，b-不饱和腈的高度对映体选择性共轭还原具有类似空间需求的芳基，并且没有二级配位点。降低了在芳基上具有间位和对位取代基的一系列底物，对映选择性很好（至97％对映体过量（ee）），并且该方法学被用于indatraline的正式合成。

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《Chemistry: A European journal》 |2009年第42期|共5页
作者
Kihyun Yoo; Hyohyun Kim; Jaesook Yun;
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正文语种 eng
中图分类应用化学;
关键词
asymmetric catalysis; copper; enantioselectivity; silanes; reduction;

机译：不对称催化;铜;对映选择性;硅烷;还原;

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1. Asymmetric Synthesis of 1,1-DiarylACHTUNGTRENUNGalkyl Units by a Copper Hydride Catalyzed Reduction: Differentiation Between Two Similar Aryl ACHTUNGTRENUNGSubstituents [J] . Kihyun Yoo, Hyohyun Kim, Jaesook Yun Chemistry: A European journal . 2009,第42期

机译：铜氢化物催化还原反应的不对称合成1,1-二芳基ACHTUNGTRENUNG烷基单元：两种相似的芳基乙酰基取代基之间的区别
2. Asymmetric synthesis of N-aryl sulfinamides: copper(I)-catalyzed coupling of sulfinamides with aryl iodides via kinetic resolution [J] . Liu Yangyuan, Wang Zesheng, Guo Bin, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2016,第22期

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3. Asymmetric synthesis of 4-aryl-1,2,5-thiadiazolidin-3-one 1,1-dioxides via Pd-catalyzed hydrogenation of cyclic ketimines [J] . Zhou-Hao Zhu, Meng-Lin Chen, Guo-Fang Jiang Organic & biomolecular chemistry . 2017,第6期

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4. Synthesis of Benzoic Acid Derivatives via Copper-Catalyzed Carboxylation of Unactivated Aryl Silanes [C] . Woo-Jin YOO, Junpei KONDO, Shu KOBAYASHI 日本化学会春季年会講演予稿集 . 2018

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5. I. Heterogeneous cross-coupling reactions catalyzed by nickel-in-charcoal and copper-in-charcoal. II. Asymmetric 1,2/1,4-reductions catalyzed by copper hydride. III. Atropselective synthesis of the biaryl A-B ring system of vancomycin utilizing an internally tethered, nonracemic ligand. [D] . Lee, Ching-Tien. 2009

机译：I.炭中镍和炭中铜催化的非均相交叉偶联反应。二。氢化铜催化的不对称1,2 / 1,4-还原反应。三，利用内部束缚的非外消旋配体进行万古霉素联芳基A-B环系统的选择性催化合成。
6. Asymmetric Catalysis Special Feature Part II: Copper-catalyzed asymmetric conjugate reduction as a route to novel β-azaheterocyclic acid derivatives [O] . Matthew P. Rainka, Yimon Aye, Stephen L. Buchwald 2004

机译：不对称催化特征第二部分：铜催化不对称共轭还原反应作为新型β-氮杂杂环酸衍生物的途径
7. Cover Picture: Asymmetric Synthesis of 1,1-Diarylalkyl Units by a Copper Hydride Catalyzed Reduction: Differentiation Between Two Similar Aryl Substituents (Chem. Eur. J. 42/2009) [O] . Kihyun Yoo, Hyohyun Kim, Jaesook Yun 2009

机译：封面图片：通过铜氢化物催化还原的1,1-二芳基烷基单元的不对称合成：两种类似芳基取代基之间的分化（Chem。欧元。J. 42/2009）

Asymmetric Synthesis of 1,1-DiarylACHTUNGTRENUNGalkyl Units by a Copper Hydride Catalyzed Reduction: Differentiation Between Two Similar Aryl ACHTUNGTRENUNGSubstituents

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