Friedel-Crafts-type alkylation in aqueous media using resin-supported peptide catalyst having polyleucine

被引：34

作者：

Akagawa, Kengo ^{[1
]}

Yamashita, Takuhiro ^{[1
]}

Sakamoto, Seiji ^{[2
]}

Kudo, Kazuaki ^{[1
]}

机构：

[1] Univ Tokyo, Inst Ind Sci, Meguro Ku, Tokyo 1538505, Japan

[2] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Aoba Ku, Sendai, Miyagi 9808577, Japan

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 40期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; CYCLIC 1,3-DICARBONYL COMPOUNDS; INDOLE ALKYLATIONS; CONSTRUCTION; ORGANOCATALYSTS; NITROALKENES; PYRROLE; ALKENES; SILICA;

D O I：

10.1016/j.tetlet.2009.07.071

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric Friedel-Crafts-type alkylation in aqueous media was realized by the resin-supported N-terminal prolyl peptide catalyst having a polyleucine tether. The hydrophobic polyleucine chain in the peptide catalyst was essential for the reaction efficiency and enantioselectivity. The resin-bound peptide catalyst could be reused at least for five times. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5602 / 5604

页数：3

共 44 条

[21]

Jorgensen KAE, 2003, SYNTHESIS-STUTTGART, P1117

[22] Highly enantioselective Friedel-Crafts reaction of 4,7-dihydroindoles with imines by chiral phosphoric acids: Facile access to 2-indolyl methanamine derivatives [J].

Kang, Qiang ;

Zheng, Xiao-Han ;

You, Shu-Li .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (12) :3539-3542

[23] Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid [J].

Kang, Qiang ;

Zhao, Zhuo-An ;

You, Shu-Li .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) :1484-+

[24] Friedel-Crafts alkylation of indoles with epoxides catalyzed by nanocrystalline titanium(IV) oxide [J].

Kantam, M. Lakshmi ;

Laha, Soumi ;

Yadav, Jagjit ;

Sreedhar, B. .

TETRAHEDRON LETTERS, 2006, 47 (35) :6213-6216

[25] Enantioselective synthesis of a highly potent selective serotonin reuptake inhibitor. An application of imidazolidinone catalysis to the alkylation of indoles with an α,β-disubstituted α,β-unsaturated aldehyde [J].

King, HD ;

Meng, ZX ;

Denhart, D ;

Mattson, R ;

Kimura, R ;

Wu, DD ;

Gao, Q ;

Macor, JE .

ORGANIC LETTERS, 2005, 7 (16) :3437-3440

[26] Enantioselective organocatalytic intramolecular ring-closing Friedel-Crafts-type alkylation of indoles [J].

Li, Chang-Feng ;

Liu, Hiu ;

Liao, Jie ;

Cao, Yi-Ju ;

Liu, Xiao-Peng ;

Xiao, Wen-Jing .

ORGANIC LETTERS, 2007, 9 (10) :1847-1850

[27] Organocatalytic enantioselective Friedel-Crafts reaction of pyrrole derivatives with imines [J].

Li, Guilong ;

Rowland, Gerald B. ;

Rowland, Emily B. ;

Antilla, Jon C. .

ORGANIC LETTERS, 2007, 9 (20) :4065-4068

[28] Organocatalytic asymmetric Friedel-Crafts alkylation/cascade reactions of naphthols and nitroolefins [J].

Liu, Tian-Yu ;

Cui, Hai-Lei ;

Chai, Qian ;

Long, Jun ;

Li, Bang-Jing ;

Wu, Yong ;

Ding, Li-Sheng ;

Chen, Ying-Chun .

CHEMICAL COMMUNICATIONS, 2007, (22) :2228-2230

[29] The enantioselective organocatalytic 1,4-addition of electron-rich benzenes to α,β-unsaturated aldehydes [J].

Paras, NA ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7894-7895

[30] New strategies in organic catalysis: The first enantioselective organocatalytic Friedel-Crafts alkylation [J].

Paras, NA ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4370-4371

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