A highly enantioselective thiolation of sulfonyl indoles to access 3-sec-sulfur-substituted indoles in water

被引：23

作者：

Chen, Ping ^{[1
,2
]}

Lu, Sheng-mei ^{[1
]}

Guo, Wengang ^{[1
,2
]}

Liu, Yan ^{[1
]}

Li, Can ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

[2] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 01期

基金：

中国国家自然科学基金;

关键词：

CARBON-CARBON BOND; BETA-SUBSTITUTED TRYPTOPHANS; FRIEDEL-CRAFTS REACTION; GENERATED IN-SITU; CONJUGATE ADDITION; TRANSFER HYDROGENATION; ARYLSULFONYL INDOLES; EMULSION DROPLETS; MICHAEL ADDITION; AQUEOUS-MEDIA;

D O I：

10.1039/c5cc07721d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective approach for the synthesis of 3-alkylindole or indoline derivatives with a functional thiol group is presented. The chemistry is based on the asymmetric 1,4-addition of thiol to vinylogous imine intermediates, which are generated in situ from sulfonylindoles. The broad substrate transformation proceeds with high yields (up to 96%) and enantioselectivity (up to 98% ee) in a water-compatible system.

引用

页码：96 / 99

页数：4

共 83 条

[41] Chiral Squaramide Derivatives are Excellent Hydrogen Bond Donor Catalysts [J].

Malerich, Jeremiah P. ;

Hagihara, Koji ;

Rawal, Viresh H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) :14416-+

[42] Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to α,β-unsaturated aldehydes [J].

Marigo, M ;

Schulte, T ;

Franzén, J ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) :15710-15711

[43] Facile and efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions [J].

Matsugi, M ;

Murata, K ;

Gotanda, K ;

Nambu, H ;

Anilkumar, G ;

Matsumoto, K ;

Kita, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07) :2434-2441

[44] Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: Inversion of configuration at C9 dramatically improves catalyst performance [J].

McCooey, SH ;

Connon, SJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (39) :6367-6370

[45]

McDaid P, 2002, ANGEW CHEM INT EDIT, V41, P338, DOI 10.1002/1521-3773(20020118)41:2<338::AID-ANIE338>3.0.CO

[46]

2-M

[47] On water: Unique reactivity of organic compounds in aqueous suspension [J].

Narayan, S ;

Muldoon, J ;

Finn, MG ;

Fokin, VV ;

Kolb, HC ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (21) :3275-3279

[48] Ultrasound-Assisted Synthesis, Anticonvulsant Activity, and Docking Study of Indole-Appended Thiazolidin-4-ones [J].

Nikalje, Anna Pratima G. ;

Shaikh, Sameer I. ;

Mulay, Abhineet ;

Khan, Firoz A. K. ;

Sangshetti, Jaiprakash N. ;

Shaikh, Shoaib .

ARCHIV DER PHARMAZIE, 2014, 347 (10) :756-767

[49] Design, synthesis, and structure-activity relationships of novel tetracyclic compounds as peripheral benzodiazepine receptor ligands [J].

Okubo, T ;

Yoshikawa, R ;

Chaki, S ;

Okuyama, S ;

Nakazato, A .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (13) :3569-3580

[50] Synthesis of 3-substituted indoles via reactive alkylideneindolenine intermediates [J].

Palmieri, Alessandro ;

Petrini, Marino ;

Shaikh, Rafik R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (06) :1259-1270

← 1 2 3 4 5 6 7 8 9 →