Cu(I)-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with 2-Aryl-N-sulfonylaziridines as Alkylating Agents

被引：43

作者：

Ge, Chen ^{[1
]}

Liu, Ren-Rong ^{[1
]}

Gao, Jian-Rong ^{[1
]}

Jia, Yi-Xia ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 13期

基金：

中国国家自然科学基金;

关键词：

CARBON QUATERNARY STEREOCENTERS; RING-OPENING REACTIONS; MESO-EPOXIDES; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; CONSTRUCTION; AZIRIDINES; DERIVATIVES; PYRROLOINDOLINES;

D O I：

10.1021/acs.orglett.6b01317

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly enantioselective Friedel-Crafts alkylation of indoles with N-sulfonylaziridines as alkylating agents has been developed by utilizing the complex of Cu-(CH3CN)(4)BF4/(S)-Segphos as a catalyst. A range of optically active tryptamine derivatives are obtained in good to excellent yields and enantioselectivities (up to >99% ee) via a kinetic resolution process.

引用

页码：3122 / 3125

页数：4

共 44 条

[1] Kinetic resolution of epoxides by a C-C bond-forming reaction:: Highly enantioselective addition of indoles to cis, trans, and meso aromatic epoxides catalyzed by [Cr(salen)] complexes [J].

Bandini, M ;

Cozzi, PG ;

Melchiorre, P ;

Umani-Ronchi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :84-87

[2] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].

Bandini, M ;

Melloni, A ;

Umani-Ronchi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556

[3] Organocatalytic strategies for the asymmetric functionalization of indoles [J].

Bartoli, Giuseppe ;

Bencivenni, Giorgio ;

Dalpozzo, Renato .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) :4449-4465

[4] Chiral scandium-catalysed enantioselective ring-opening of meso-epoxides with N-heterocycle, alcohol and thiol derivatives in water [J].

Boudou, Marine ;

Ogawa, Chikako ;

Kobayashi, Shu .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (18) :2585-2589

[5] Copper(I)-Catalyzed Kinetic Resolution of N-Sulfonylaziridines with Indoles: Efficient Construction of Pyrroloindolines [J].

Chai, Zhuo ;

Zhu, You-Min ;

Yang, Pei-Jun ;

Wang, Shaoyin ;

Wang, Shaowu ;

Liu, Zhen ;

Yang, Gaosheng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (32) :10088-10091

[6] Enantioselective Synthesis and Stereoselective Ring Opening of N-Acylaziridines [J].

Cockrell, Jennifer ;

Wilhelmsen, Christopher ;

Rubin, Heather ;

Martin, Allen ;

Morgan, Jeremy B. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (39) :9842-9845

[7] Highly Enantioselective Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters via Nickel-Catalyzed Friedel-Crafts Alkylation Reaction [J].

Gao, Jian-Rong ;

Wu, Hao ;

Xiang, Bin ;

Yu, Wu-Bin ;

Han, Liang ;

Jia, Yi-Xia .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (08) :2983-2986

[8] Lewis Acid Catalyzed SN2-Type Ring Opening of N-Activated Aziridines with Electron-Rich Arenes/Heteroarenes [J].

Ghorai, Manas K. ;

Tiwari, Deo Prakash ;

Jain, Nikita .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14) :7121-7130

[9] Enantioselective construction of a 2,2′-bisindolylmethane scaffold via catalytic asymmetric reactions of 2-indolylmethanols with 3-alkylindoles [J].

Gong, Yu-Xin ;

Wu, Qiong ;

Zhang, Hong-Hao ;

Zhua, Qiu-Ning ;

Shi, Feng .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (29) :7993-8000

[10] Catalytic enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes by using a simple thiourea organocatalyst [J].

Herrera, RP ;

Sgarzani, V ;

Bernardi, L ;

Ricci, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (40) :6576-6579

← 1 2 3 4 5 →