Organocatalytic Regio- and Enantioselective Allylic Alkylation of Indolin-2-imines with MBH Carbonates toward 3-Allylindoles

被引：7

作者：

Chen, Lunfeng ^{[1
]}

Li, Pengfei ^{[2
,3
]}

机构：

[1] Harbin Inst Technol, Sch Resources & Environm, Harbin 150080, Peoples R China

[2] Southern Univ Sci & Technol SUSTech, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China

[3] Southern Univ Sci & Technol SUSTech, Coll Sci, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 12期

基金：

中国国家自然科学基金;

关键词：

REGIOSELECTIVE SYNTHESIS; ALPHA-CARBOLINES; INDOLES; FUNCTIONALIZATION; SUBSTITUTION; LIGANDS; HETEROCYCLES; ALLYLATION; ANNULATION; STRATEGIES;

D O I：

10.1021/acs.joc.2c02310

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An organocatalytic asymmetric C3-allylic alkylation of indolone-2-imines with MBH carbonates has been developed for the first time. As opposed to previous reports, an "interrupted" annulation was achieved, affording 3-allylindoles in generally high yields with excellent stereoselectivities. The representative scale-up reaction and transformation of 3-allylindoles were examined. A possible mechanism was also proposed.

引用

页码：7810 / 7814

页数：5

共 6 条

[1] Enantioselective Synthesis of 3-Allylindoles from Indolin-2-imines and MBH Carbonates via Nucleophilic Catalysis
Chen, Lunfeng
Li, Pengfei
CHEMISTRYSELECT, 2024, 9 (06):
[2] Palladium-Catalyzed Regioselective C3-Allylic Alkylation of 2-Aryl Imidazopyridines with MBH Carbonates
Murugesan, Tamilarasu
Elikkottil, Afna
Kaliyamoorthy, Alagiri
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (04) : 2655 - 2665
[3] Bifunctional Bronsted Base Catalyzed [3+3] Annulations of Indolin-2-imines and α,β-Unsaturated Imides: An Enantioselective Approach to α-Carbolinones
Chen, Lin
Zhang, Xiang
Shi, Ke-Jin
Leng, Hai-Jun
Li, Qing-Zhu
Liu, Yu
Li, Jiang-Hong
Wang, Qi-Wei
Li, Jun-Long
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (15) : 9454 - 9463
[4] Ir-Catalyzed Chemo-, Regio-, and Enantioselective Allylic Enolization of 6,6-Dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one Involving Keto-Enol Isomerization
Wang, Xiao-Lin
Chen, Ji-Teng
Zheng, Sheng-Cai
Zhao, Xiao-Ming
MOLECULES, 2022, 27 (20):
[5] Organocatalytic Asymmetric Allylic Alkylation of Morita-Baylis-Hillman Carbonates with Phosphorus Ylides: Synthesis of Chiral 3-Substituted 2,4-Functionalized 1,4-Pentadienes
Lin, Aijun
Wang, Junying
Mao, Haibin
Shi, Yan
Mao, Zhijie
Zhu, Chengjian
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (28) : 6241 - 6245
[6] Regio- and diastereoselective construction of 1′,2′-(dihydrospiro[indoline-3,3′-pyrrol]-2′-yl)acrylates through phosphine-catalyzed [4+1] annulation of Morita-Baylis-Hillman carbonates with oxindole-derived α, β-unsaturated imines
Lei, Yu
Zhang, Xiao-Nan
Yang, Xue-Yan
Xu, Qin
Shi, Min
RSC ADVANCES, 2015, 5 (61) : 49657 - 49661

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