Synthesis of C5-Allylindoles through an Iridium-Catalyzed Asymmetric Allylic Substitution/Oxidation Reaction Sequence of N-Alkyl Indolines

被引：13

作者：

Lu, Jiamin ^{[1
]}

Xu, Ruigang ^{[1
]}

Zeng, Haixia ^{[1
]}

Zhong, Guofu ^{[1
]}

Wang, Meifang ^{[1
]}

Ni, Zhigang ^{[1
]}

Zeng, Xiaofei ^{[1
]}

机构：

[1] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 311121, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 09期

关键词：

ENANTIOSELECTIVE SYNTHESIS; INDOLES; ALLYLATION; FUNCTIONALIZATION; DEAROMATIZATION; ARYLATION; ALCOHOLS; DERIVATIVES; C5;

D O I：

10.1021/acs.orglett.1c00810

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Iridium/Bronsted acid cooperative catalyzed asymmetric allylic substitution reactions at the C5 position of indolines have been reported for the first time. The highly efficient protocol allows rapid access to various C5-allylated products in good to high yields (48-97%) and enantioselectivities (82% to >99% ee) with wide functional group tolerance. The transformations allow not only the formation of C5-allylindoline derivatives but also the synthesis of C5-allylindole analogues in good yields and excellent stereoselectivities via an allylation/oxidation reaction sequence.

引用

页码：3426 / 3431

页数：6

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