Highly efficient synthesis of chiral quaternary 3-aminooxindoles promoted by zinc(II) chloride via Et2Zn-catalysed addition of Grignard reagents to isaltin-derived N-tert-butanesulfinyl ketimines

Shiwei Yang; Guangling Bian; Zhongxiang Chen; Xiaohan Xia; Mi Zhou; Caiyan Cui; Ling Song

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Highly efficient synthesis of chiral quaternary 3-aminooxindoles promoted by zinc(II) chloride via Et₂Zn-catalysed addition of Grignard reagents to isaltin-derived N-tert-butanesulfinyl ketimines

机译：通过 Et _{2 Zn催化的格氏试剂向异麦草碱衍生的 N-叔胺加成反应，高效合成氯化锌（em）促进的手性季铵基3-氨基羟吲哚-丁烷亚磺酰基酮亚胺}

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A highly efficient and practical approach to chiral quaternary 3-aminooxindoles was developed via Et₂Zn catalyzed diastereoselective addition of Grignard reagents to isaltin-derived N-tert-butanesulfinyl ketimines giving good to excellent yields and diastereoselectivities with broad substrates and reagent scopes promoted by zinc(II) chloride. 展开▼

机译：通过 Et _{2 Zn催化格氏试剂非对映选择性加成到胰岛素衍生的上，开发了一种高效且实用的手性季铵基3-氨基氧吲哚。 em> N-叔-丁亚砜基酮亚胺具有优异的收率和非对映选择性，具有广泛的底物和氯化锌（ II ）促进的试剂范围。} 展开▼

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《RSC Advances》 |2017年第61期|共4页

作者
Shiwei Yang; Guangling Bian; Zhongxiang Chen; Xiaohan Xia; Mi Zhou; Caiyan Cui; Ling Song;
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中图分类化学;

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专利

1. Zn-mediated asymmetric allylation of N-tert-butanesulfinyl ketimines: an efficient and practical access to chiral quaternary 3-aminooxindoles [J] . Diao Chen, Ming-Hua Xu Chemical Communications . 2013,第13期

机译：锌介导的N-叔丁烷亚磺酰基酮亚胺的不对称烯丙基化：一种有效，实用的手性季铵3-氨基羟吲哚。

2. Highly Regio- and Diastereoselective Addition of Organolithium Reagents to Chiral Fluoroalkyl alpha,beta-Unsaturated N-tert-Butanesulfinyl Ketimines: A General and Efficient Access to alpha-Tertiary Fluoroalkyl Allylic Amines and alpha-Fluoroalkyl alpha-Amino Acids [J] . Liu Peng, Liu Zhen-Jiang, Wu Fanhong Advanced synthesis & catalysis . 2015,第4期

机译：有机锂试剂向手性氟烷基α，β-不饱和N-叔丁亚磺酰基酮亚胺的高度区域和非对映选择性加成：α-叔氟烷基烯丙基胺和α-氟烷基α-氨基酸的通用有效途径

3. Highly Diastereoselective Addition of Alkynylmagnesium Chlorides to N-tert Butanesulfinyl Aldimines: A Practical and General Access to Chiral a-Branched Amines [J] . Bai-Ling Chen, Bing Wang, Guo-Qiang Lin The Journal of Organic Chemistry . 2010,第3期

机译：N-叔丁烷亚磺酰基醛亚胺中高度非对映选择性的烷基氯化铝：手性α-支化胺的实用和通用途径

4. Highly Efficient Alkylation to Ketones with Grignard Reagents Catalyzed by Zinc(II) Chloride [C] . Manabu Hatano, Shinji Suzuki, Kazuaki Ishihara Symposium on Organometallic Chemistry . 2006

机译：用锌（II）氯化锌催化的GRIGNARD试剂对酮高效的烷基化

5. Part I: Copper(I) iodide dimethyl sulfide catalyzed 1,4-addition of alkenyl groups from alkenylzirconium and alkenylzinc reagents and their application toward the total synthesis of azaspirene, and, Part II: Aqueous Wittig chemistry employing stabilized ylides and aldehydes [D] . El-Batta, Amer Adnan 2007

机译：第一部分：碘化亚铜（I）二甲基硫醚从烯基锆和烯基锌试剂中催化烯基的1，4-加成反应及其在氮杂螺碳烯的全合成中的应用，第二部分：采用稳定化的乙炔和醛的水维蒂希化学

6. Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers by Catalytic Asymmetric Conjugate Additions of Alkyl and Aryl Aluminum Reagents to Five- Six- and Seven-Membered-Ring β-Substituted Cyclic Enones [O] . Tricia L. May, M. Kevin Brown, Amir H. Hoveyda -1

机译：烷基和芳烃铝试剂催化不对称共轭加成五元六元和七元环β-取代的环烯酮的全碳四元立体中心的对映选择性合成

7. Tandem Addition/Cyclization Reaction of Organozinc Reagents to 2-Alkynyl Aldehydes: Highly Efficient Regio- and Enantioselective Synthesis of 1,3-Dihydroisobenzofurans and Tetrasubstituted Furans [O] . -1

机译：有机辛试剂对2-炔基醛的串联添加/环化反应：1,3-二羟基异呋喃和四氢呋喃的高效序列和对映选择性合成

8. Enolboration 7. Dicyclohexyliodoborane, a Highly Stereoselective Reagent For theEnolboration Of Tertiary Amides. Effects of Solvent And Aldolization Temperature on Stereochemistry Achieving the Stereoselective Synthesis of Either Syn or Anti Aldols [R] . Ganesan, K., Brown, H. C. 1994

机译：配合7.二环己基碘硼烷，一种高立体选择性试剂，用于叔酰胺的合成。溶剂和醛醇化温度对立体化学实现syn或anti aldols立体选择性合成的影响

1. COMPLEXES OF O-ALKYLGUANYLISOUREA WITH ZINC CHLORIDE AS PARENT REAGENTS FOR SYNTHESIS OF 6-AMINO-4-ALKOXY-2-ALKYL-1,3,5-TRIAZINES - SEMIPRODUCTS FOR HERBICIDE SYNTHESIS [P] . 外国专利： SU1293972A1 . 1997-01-10

机译：O-烷基胍基脲与氯化锌的配位化合物的配位化合物，用于合成6-氨基-4-烷基-2-烷基-1,3,5-三嗪-合成除草剂的半成品

2. ETHANOL OR HIGHER ALCOHOL SYNTHESIS CATALYST COMPRISING A CRYSTALLINE HYDROXYCARBONATE, COPPER, ZINC, AT LEAST ONE ELEMENT FROM GROUPS IIIA, IIIB, IVB AND VIIB AND ONE ELEMENT FROM AL, MG AND CR, USE THEREOF [P] . 外国专利： NZ263254A . 1998-06-26

机译：乙醇或高级醇合成催化剂，含羟基碳酸盐，铜，锌，锌，至少来自IIIA，IIIB，IVB和VIIB组元素，以及来自AL，MG和CR的一种元素

3. HIGHLY EFFICIENT HEAT DISSIPATION COIL AND HIGHLY EFFICIENT HEAT DISSIPATION MOTOR EMPLOYING THEREOF, HIGHLY EFFICIENT HEAT DISSIPATION POWER SUPPLY DEVICE, HIGHLY EFFICIENT HEAT DISSIPATION MAGNETRON GENERATOR, AND ELECTRONIC APPARATUS, INDUSTRIAL APPARATUS, ELECTRICAL HOME APPLIANCE, COMPUTER HARD DISK PRODUCT, AND ELECTRIC VEHICLE EMPLOYING THE COIL, MOTOR AND DEVICES [P] . 外国专利： JP2009153366A . 2009-07-09

机译：高效散热线圈和高效散热电机，使用高效散热耗电电源设备，高效散热磁控发电机，电子电器，电器，家用电器，工业设备线圈，马达和设备

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Highly efficient synthesis of chiral quaternary 3-aminooxindoles promoted by zinc(II) chloride via Et2Zn-catalysed addition of Grignard reagents to isaltin-derived N-tert-butanesulfinyl ketimines

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Highly efficient synthesis of chiral quaternary 3-aminooxindoles promoted by zinc(II) chloride via Et₂Zn-catalysed addition of Grignard reagents to isaltin-derived N-tert-butanesulfinyl ketimines