Iridium-Catalyzed Enantioselective and Diastereoselective Allylation of Dioxindoles: A One-Step Synthesis of 3-AllyI-3-hydroxyoxindoles

被引：30

作者：

He, Rui ^{[1
]}

Wu, Shanchao ^{[1
]}

Tang, Haoming ^{[1
]}

Huo, Xiaohong ^{[1
]}

Sun, Zhenliang ^{[2
]}

Zhang, Wanbin ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

[2] Shanghai Jiao Tong Univ, Peoples Hosp 6, South Campus,6600 Nanfeng Rd, Shanghai 201499, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 19期

关键词：

DIASTEREODIVERGENT ALPHA-ALLYLATION; ALLYLIC SUBSTITUTION-REACTIONS; VINYLOGOUS ALDOL REACTION; IR/ZN DUAL CATALYSIS; ASYMMETRIC ALLYLATION; SYNERGISTIC IRIDIUM; TERTIARY ALCOHOLS; DIRECT ACCESS; AMINO-ACIDS; ISATINS;

D O I：

10.1021/acs.orglett.8b02655

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iridium-catalyzed asymmetric allylation of dioxindoles, 3-hydroxyoxindoles, regulated by prosthetic groups has been accomplished under mild conditions. The methodology is applicable to a diverse array of 3-hydroxyoxindole and cinnamyl acetate substrates. A range of 3-ally'-3-hydroxyoxindoles containing vicinal tetrasubstituted and trisubstituted stereocenters can be efficiently synthesized in one-step with excellent enantioselectivity (up to >99% enaniomeric excess (ee)) and good diastereoselectivity (up to 11:1 diastereomeric ratio (dr)).

引用

页码：6183 / 6187

页数：5

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