Indolylmethanols as Reactants in Catalytic Asymmetric Reactions

被引:149
作者
Mei, Guang-Jian [1 ]
Shi, Feng [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Peoples R China
基金
中国国家自然科学基金;
关键词
BRONSTED-ACID CATALYSIS; TETRAHYDRO-BETA-CARBOLINE; FRIEDEL-CRAFTS REACTION; DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; PHOSPHORIC-ACID; ALPHA-ALKYLATION; FLUORENE DERIVATIVES; INDOL-2-YL CARBINOLS; INDOLE-DERIVATIVES;
D O I
10.1021/acs.joc.7b01458
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Indolylmethanols have emerged as versatile reactants in catalytic asymmetric reactions because of the facile generation of reactive intermediates from these compounds. The most common indolylmethanols are 3-indolylmethanols and 2-indolylmethanols, and the reaction types applicable to these heterocycles mainly include catalytic enantioselective substitutions and cyclizations. Using indolylmethanols as reactants in catalytic asymmetric reactions enables the enantioselective construction of a variety of indole-containing frameworks.
引用
收藏
页码:7695 / 7707
页数:13
相关论文
共 76 条
[1]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[2]   Stronger Bronsted Acids: Recent Progress [J].
Akiyama, Takahiko ;
Mori, Keiji .
CHEMICAL REVIEWS, 2015, 115 (17) :9277-9306
[3]   Electrophilicity: the "dark-side" of indole chemistry [J].
Bandini, Marco .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (32) :5206-5212
[4]   Bronsted Acid Catalyzed [3+2]-Cycloaddition of Cyclic Enamides with in Situ Generated 2-Methide-2H-indoles: Enantioselective Synthesis of Indolo[1,2-a]indoles [J].
Bera, Kalisankar ;
Schneider, Christoph .
ORGANIC LETTERS, 2016, 18 (21) :5660-5663
[5]   Bronsted Acid Catalyzed [3+2]-Cycloaddition of 2-Vinylindoles with In Situ Generated 2-Methide-2H-indoles: Highly Enantioselective Synthesis of Pyrrolo[1,2-a]indoles [J].
Bera, Kalisankar ;
Schneider, Christoph .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (21) :7074-7078
[6]   Organocatalytic Asymmetric Alkylation of Aldehydes by SN1-Type Reaction of Alcohols [J].
Cozzi, Pier Giorgio ;
Benfatti, Fides ;
Zoli, Luca .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (07) :1313-1316
[7]   Diastereo- and Enantioselective Construction of a Bispirooxindole Scaffold Containing a Tetrahydro-β-carboline Moiety through an Organocatalytic Asymmetric Cascade Reaction [J].
Dai, Wei ;
Lu, Han ;
Li, Xin ;
Shi, Feng ;
Tu, Shu-Jiang .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (36) :11382-11389
[8]   The Diarylprolinol Silyl Ethers: Ten Years After [J].
Donslund, Bjarke S. ;
Johansen, Tore Kiilerich ;
Poulsen, Pernille H. ;
Halskov, Kim Soholm ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) :13860-13874
[9]   An Enantioselective Approach to 2,3-Disubstituted Indolines through Consecutive Bronsted Acid/Pd-Complex-Promoted Tandem Reactions [J].
Duan, Ying ;
Chen, Mu-Wang ;
Ye, Zhi-Shi ;
Wang, Duo-Sheng ;
Chen, Qing-An ;
Zhou, Yong-Gui .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (26) :7193-7197
[10]   The Application of N-Protected 3-Vinylindoles in Chiral Phosphoric Acid-Catalyzed [3+2] Cyclization with 3-Indolylmethanols: Monoactivation of the Catalyst to Vinyliminium [J].
Fan, Tao ;
Zhang, Hong-Hao ;
Li, Can ;
Shen, Yang ;
Shi, Feng .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (12) :2017-2031