Development of the Regiodivergent Asymmetric Prenylation of 3-Substituted Oxindoles

Barry M. Trost; Walter H. Chan; Sushant Malhotra

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Development of the Regiodivergent Asymmetric Prenylation of 3-Substituted Oxindoles

机译：三种取代氧胆管的直流不对戊烯化的发展

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This paper describes our efforts to design a Pdcatalyzed asymmetric prenylation of 3-substituted oxindoles that affords access to both the linear and reverse-prenylated products. Both 3-alkyl- and 3-aryloxindoles performed well under our optimized reaction conditions. The regiodivergent alkylation of monoterpene-derived electrophiles using this methodology was also investigated. The utility of this methodology in natural product synthesis was demonstrated through the efficient total syntheses of four Flustra alkaloids, which also allowed the absolute stereochemistry of the prenylated oxindole products to be assigned. Surprisingly, the same enantiomer of ligand produced linear and branched regioisomers of opposite chirality.

机译：本文介绍了我们设计3取代的氧胆碱的PDCAtalyzed不对称戊烯化，其提供直线和戊烯化产物的可接近的。在我们的优化反应条件下，3-烷基和3-芳氧吲哚溶解均匀。还研究了使用该方法的单萜衍生的电子手机的直流烷基化。通过有效的四种福利生物碱的有效合成来证明了本方法在天然产物合成中的效用，其还允许分配戊酰化的氧吲哚产物的绝对立体化学。令人惊讶的是，配体的相同对映体产生了相反的手性的线性和支链的征收体。

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来源
《Chemistry: A European journal》 |2017年第18期|共10页
作者
Barry M. Trost; Walter H. Chan; Sushant Malhotra;
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作者单位

Department of Chemistry Stanford University Stanford CA 94305 (USA);

University of Toronto 78 Queens Park Toronto ON M5S 2C5 (Canada);

Discovery Chemistry Genentech 1 DNA Way South San Francisco CA 94080 (USA);

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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
allylic alkylation; flustramines; oxindoles; palladium; prenylation;

机译：allylic烷基化;投产;氧胆汁;钯;戊烯;

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专利

1. Development of the Regiodivergent Asymmetric Prenylation of 3-Substituted Oxindoles [J] . Barry M. Trost, Walter H. Chan, Sushant Malhotra Chemistry: A European journal . 2017,第18期

机译：三种取代氧胆管的直流不对戊烯化的发展
2. Iridium-catalyzed asymmetric hydrogenation of 3-substituted unsaturated oxindoles to prepare C3-mono substituted oxindoles [J] . Liu Y., Yao D., Li K., Tetrahedron . 2011,第44期

机译：铱催化的3-取代不饱和羟吲哚的不对称加氢反应制备C3-单取代羟吲哚
3. Highly enantioselective synthesis of 3-amino-2-oxindole derivatives: Catalytic asymmetric α-amlnation of 3-substituted 2-oxindoles with a chiral scandium complex [J] . Yang Z., Wang Z., Bai S., Chemistry: A European journal . 2010,第22期

机译：3-氨基-2-氧吲哚衍生物的高度对映选择性合成：3-取代的2-氧吲哚与手性scan配合物的催化不对称α-接枝
4. Helically Chiral Nucleophilic Polymer Catalyst for Asymmetric Acyl Rearrangement of Oxindole Derivatives [C] . Takuya Takahashi, Ryo Murakami, Takeshi Yamamoto 日本化学会春季年会講演予稿集 . 2018

机译：用于氧吲哚衍生物的不对称酰基重排的螺旋手性亲核聚合物催化剂
5. Asymmetric synthesis of all-carbon alpha-aryl quaternary carbonyl compounds by palladium-catalyzed asymmetric allylic alkylation (Pd-AAA) and their application to the synthesis of biologically important 3,3 '-disubstituted oxindole and alpha-disubstituted quaternary beta-lactone frameworks. [D] . Asad, Md. Sharif A. 2015

机译：钯催化的不对称烯丙基烷基化反应（Pd-AAA）的全碳α-芳基季羰基化合物的不对称合成及其在生物学上重要的3,3'-二取代的羟吲哚和α-二取代的季铵β-内酯骨架的合成中。
6. Development of the Regiodivergent Asymmetric Prenylation of 3-Substituted Oxindoles [O] . Prof. Dr. Barry M. Trost, Dr. Walter H. Chan, Dr. Sushant Malhotra -1

机译：取代3-吲哚的区域发散性不对称烯丙基的发展
7. Development of the Regiodivergent Asymmetric Prenylation of 3‐Substituted Oxindoles [O] . Barry M. Trost, Walter H. Chan, Sushant Malhotra 2017

机译：三种取代的氧胆管的直流不对戊烯化的发展

Development of the Regiodivergent Asymmetric Prenylation of 3-Substituted Oxindoles

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