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

被引：11

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

共 73 条

[61] Hg(OTf)2-BINAPHANE-Catalyzed Enantioselective Anilino Sulfonamide Allyl Alcohol Cyclization [J].

Yamamoto, Hirofumi ;

Ho, Elisabeth ;

Namba, Kosuke ;

Imagawa, Hiroshi ;

Nishizawa, Mugio .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (37) :11271-11274

[62] Iridium-catalyzed, asymmetric amination of allylic alcohols activated by Lewis acids [J].

Yamashita, Yasuhiro ;

Gopalarathnam, Apsara ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7508-+

[63] Organocatalytic stereoselective cationic polymerization of vinyl ethers by employing a confined bronsted acid as the catalyst [J].

Yang, Zan ;

Zhang, Xun ;

Jiang, Yu ;

Ma, Qiang ;

Liao, Saihu .

SCIENCE CHINA-CHEMISTRY, 2022, 65 (02) :304-308

[64] Kinetic Resolution of Tertiary Allylic Alcohols: Highly Enantioselective Access to Cyclic Ethers Bearing an α-Tetrasubstituted Stereocenter [J].

Zhang, Chao-Huan ;

Gao, Qing ;

Li, Meng ;

Wang, Jian-Fei ;

Yu, Chuan-Ming ;

Mao, Bin .

ORGANIC LETTERS, 2021, 23 (10) :3949-3954

[65] Strong and Confined Acids Catalyze Asymmetric Intramolecular Hydroarylations of Unactivated Olefins with Indoles [J].

Zhang, Pinglu ;

Tsuji, Nobuya ;

Ouyang, Jie ;

List, Benjamin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (02) :675-680

[66] Progress of Nucleophilic Substitution of Allylic Alcohols [J].

Zhang, Xiaoxiang ;

Sun, Xiaoping ;

Tan, Jihuai ;

Fan, Hui ;

Rao, Weidong .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (10) :2049-2058

[67] Organocatalytic, Stereoselective, Cationic Reversible Addition-Fragmentation Chain-Transfer Polymerization of Vinyl Ethers [J].

Zhang, Xun ;

Yang, Zan ;

Jiang, Yu ;

Liao, Saihu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (02) :679-684

[68] Recent advances in the annulation of Morita-Baylis-Hillman adducts [J].

Zhong, Neng-Jun ;

Wang, Yi-Zhan ;

Cheng, Liang ;

Wang, Dong ;

Liu, Li .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (29) :5214-5227

[69] Chiral Primary Amine/Palladium Dual Catalysis for Asymmetric Allylic Alkylation of β-Ketocarbonyl Compounds with Allylic Alcohols [J].

Zhou, Han ;

Zhang, Long ;

Xu, Changming ;

Luo, Sanzhong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (43) :12645-12648

[70] The Silicon-Hydrogen Exchange Reaction: Catalytic Kinetic Resolution of 2-Substituted Cyclic Ketones [J].

Zhou, Hui ;

Zhang, Pinglu ;

List, Benjamin .

SYNLETT, 2021, 32 (19) :1953-1956

← 1 2 3 4 5 6 7 8 →