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：

国家重点研发计划; 中国国家自然科学基金;

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

[1] Transition-Metal-Catalyzed Suzuki-Miyaura-Type Cross-Coupling Reactions of π-Activated Alcohols [J].

Akkarasamiyo, Sunisa ;

Ruchirawat, Somsak ;

Ploypradith, Poonsaksi ;

Samec, Joseph S. M. .

SYNTHESIS-STUTTGART, 2020, 52 (05) :645-659

[2] Confinement-Controlled, Either syn- or anti-Selective Catalytic Asymmetric Mukaiyama Aldolizations of Propionaldehyde Enolsilanes [J].

Amatov, Tynchtyk ;

Tsuji, Nobuya ;

Maji, Rajat ;

Schreyer, Lucas ;

Zhou, Hui ;

Leutzsch, Markus ;

List, Benjamin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (36) :14475-14481

[3] Unactivated Alkyl Halides in Transition-Metal-Catalyzed C-H Bond Alkylation [J].

Ankade, Shidheshwar B. ;

Shabade, Anand B. ;

Soni, Vineeta ;

Punji, Benudhar .

ACS CATALYSIS, 2021, 11 (06) :3268-3292

[4] Mechanistic Insights into Enantioselective Gold-Catalyzed Allylation of Indoles with Alcohols: The Counterion Effect [J].

Bandini, Marco ;

Bottoni, Andrea ;

Chiarucci, Michel ;

Cera, Gianpiero ;

Miscione, Gian Pietro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (51) :20690-20700

[5] Gold-Catalyzed Direct Activation of Allylic Alcohols in the Stereoselective Synthesis of Functionalized 2-Vinyl-Morpholines [J].

Bandini, Marco ;

Monari, Magda ;

Romaniello, Alessandro ;

Tragni, Michele .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (48) :14272-14277

[6] Enantioselective Gold-Catalyzed Allylic Alkylation of Indoles with Alcohols: An Efficient Route to Functionalized Tetrahydrocarbazoles [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) :9533-9537

[7] π-Activated alcohols: an emerging class of alkylating agents for catalytic Friedel-Crafts reactions [J].

Bandini, Marco ;

Tragni, Michele .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (08) :1501-1507

[8] Cooperative Catalysis by Palladium and a Chiral Phosphoric Acid: Enantioselective Amination of Racemic Allylic Alcohols [J].

Banerjee, Debasis ;

Junge, Kathrin ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (48) :13049-13053

[9] Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates [J].

Butt, Nicholas A. ;

Zhang, Wanbin .

CHEMICAL SOCIETY REVIEWS, 2015, 44 (22) :7929-7967

[10] Merging Organocatalysis with an Indium(III)-Mediated Process: A Stereoselective α-Alkylation of Aldehydes with Allylic Alcohols [J].

Capdevila, Montse Guiteras ;

Benfatti, Fides ;

Zoli, Luca ;

Stenta, Marco ;

Cozzi, Pier Giorgio .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (37) :11237-11241

← 1 2 3 4 5 6 7 8 →