Chiral Bronsted Acid-Catalyzed Intramolecular Asymmetric Allylic Alkylation of Indoles with Primary Alcohols

被引：6

作者：

Zou, Lei-Ming ^{[1
,2
]}

Huang, Xian-Yun ^{[1
,2
]}

Zheng, Chao ^{[2
]}

Cheng, Yuan-Zheng ^{[2
]}

You, Shu-Li ^{[1
,2
]}

机构：

[1] East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 19期

基金：

中国国家自然科学基金; 国家重点研发计划;

关键词：

PHOSPHORIC-ACID; NUCLEOPHILIC-SUBSTITUTION; DUAL CATALYSIS; IRIDIUM; ALLYLATION; ALDEHYDES; PALLADIUM; AMINATION; GOLD; DEAROMATIZATION;

D O I：

10.1021/acs.orglett.2c01253

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, chiral Bronsted acid-catalyzed intramolecular asymmetric allylic alkylation of indoles with allylic primary alcohols is described. The allyl alcohols were directly employed as the allylic precursors in this metal-free protocol, without preactivation or any additional activating reagents. This method provides the convenient synthesis of a broad range of functionalized tetrahydrocarbazoles in excellent yields (<= 97%) with good enantioselectivity (<= 93% ee). The optimal conditions are compatible for gram-scale reaction.

引用

页码：3544 / 3548

页数：5

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