Scandium-Catalyzed Asymmetric 1,6-Addition of 3-Substituted Oxindoles to Linear Dienyl Ketones

Wang Zhen; Kang Tengfei; Yao Qian; Ji Jie; Liu Xiaohua; Lin Lili; Feng Xiaoming

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Scandium-Catalyzed Asymmetric 1,6-Addition of 3-Substituted Oxindoles to Linear Dienyl Ketones

机译：dium催化的3-取代的吲哚向线性二烯基酮的不对称1,6-加成反应

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The first example of a N,N-dioxide-Sc-III-catalyzed 1,6-addition of 3-substituted oxindoles to dienyl ketones has been developed. This procedure tolerates a relatively wide range of 3-substituted oxindoles under mild conditions, facilitating the preparation of various chiral oxindoles with quaternary stereocenters. In addition, the reliable catalyst was found to be effective in the asymmetric 1,6-addition of both -unsubstituted and -methyl-substituted dienyl ketones, achieving excellent regioselectivities and enantioselectivities (up to>99% ee).

机译：已经开发出N，N-二氧化物-Sc-III催化的3-取代的羟吲哚与二烯基酮的1，6-加成的第一个实例。该方法在温和条件下可耐受相对广泛的3-取代的羟吲哚，从而有利于制备具有四级立体中心的各种手性羟吲哚。另外，发现可靠的催化剂对于-未取代的和-甲基取代的二烯基酮的不对称1，6-加成是有效的，实现了优异的区域选择性和对映选择性（高达＞ 99％ee）。

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《Chemistry: A European journal》 |2015年第21期|共4页
作者
Wang Zhen; Kang Tengfei; Yao Qian; Ji Jie; Liu Xiaohua; Lin Lili; Feng Xiaoming;
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正文语种 eng
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1; 6-addition reaction; asymmetric catalysis; diastereoselectivity; N; N '-dioxides; scandium;

机译：1;6-加成反应;不对称催化;非对映选择性;N;N'-二氧化物;scan;

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1. Scandium-Catalyzed Asymmetric 1,6-Addition of 3-Substituted Oxindoles to Linear Dienyl Ketones [J] . Wang Zhen, Kang Tengfei, Yao Qian, Chemistry: A European journal . 2015,第21期

机译：dium催化的3-取代的吲哚向线性二烯基酮的不对称1,6-加成反应
2. Organocatalytic asymmetric Michael addition of 3-substituted oxindoles to α,β-unsaturated acyl phosphonates for the synthesis of 3,3′-disubstituted oxindoles with chiral squaramides [J] . Lin Chen, Yong You, Ming-Liang Zhang, Organic & biomolecular chemistry . 2015,第15期

机译：3-取代的吲哚到α，β-不饱和酰基膦酸酯的有机催化不对称迈克尔加成反应，以合成具有手性方酰胺的3,3'-二取代的羟吲哚
3. Enantioselective Construction of Cyclic Enaminone-Based 3-Substituted 3-Amino-2-oxindole Scaffolds via Catalytic Asymmetric Additions of Isatin-Derived Imines [J] . Zhou Lu-Jia, Zhang Yu-Chen, Jiang Fei, Advanced synthesis & catalysis . 2016,第19期

机译：伊斯兰衍生的亚胺催化不对称加成的环烯胺基的3-取代的3-氨基-2-氧吲哚支架的对映选择性构建。
4. Rhodium-Catalyzed Asymmetric 1,6-Addition of Aryltitanates to 1,3-Enynyl Ketones.Catalytic Asymmetric Synthesis of Axially Chiral Allenes [C] . Norihito Tokunaga, Kazuya Inoue, Tamio Hayashi Symposium on Organometallic Chemistry . 2003

机译：铑催化的不对称1,6-加入芳基酸酯至1,3-烯基酮。催化不对称合成轴向手性血症
5. I. Catalytic asymmetric addition of organozinc reagents to ketones. II. Novel 1-alkenyl-1,1-bimetallic reagents: Generation and synthetic applications [D] . Li, Hongmei 2007

机译：I.有机锌试剂向酮的催化不对称加成。二。新型1-烯基-1,1-双金属试剂：生成和合成应用
6. Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 14-naphthoquinone [O] . Jin-Sheng Yu, Feng Zhou, Yun-Lin Liu, 2012

机译：未保护的3-取代的羟吲哚的有机催化不对称迈克尔加成至14-萘醌
7. Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone [O] . Jin-Sheng Yu, Feng Zhou, Yun-Lin Liu, 2012

机译：有机催化不对称迈克尔加成未受保护的3-取代氧吲哚到1,4-萘醌

Scandium-Catalyzed Asymmetric 1,6-Addition of 3-Substituted Oxindoles to Linear Dienyl Ketones

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