Chiral primary amino alcohol organobase catalysts for the asymmetric Diels-Alder reactions of anthrones with maleimides

被引：24

作者：

Kumagai, Jun ^{[1
]}

Otsuki, Teppei ^{[1
]}

Reddy, U. V. Subba ^{[1
]}

Kohari, Yoshihito ^{[1
]}

Seki, Chigusa ^{[1
]}

Uwai, Koji ^{[1
]}

Okuyama, Yuko ^{[2
]}

Kwon, Eunsang ^{[3
]}

Tokiwa, Michio ^{[4
]}

Takeshita, Mitsuhiro ^{[4
]}

Nakano, Hiroto ^{[1
]}

机构：

[1] Muroran Inst Technol, Grad Sch Engn, Div Sustainable & Environm Engn, Muroran, Hokkaido 0508585, Japan

[2] Tohoku Pharmaceut Univ, Aoba Ku, Sendai, Miyagi 9818558, Japan

[3] Tohoku Univ, Grad Sch Sci, Res & Analyt Ctr Giant Mol, Aoba Ku, Sendai, Miyagi 9808578, Japan

[4] Tokiwakai Grp, Iwaki, Fukushima 9738053, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 24期

关键词：

C-2-CHIRAL PYRROLIDINES; ORGANOCATALYSIS; ALDEHYDES; 1,2-DIHYDROPYRIDINES; CYCLOADDITION; PROLINE;

D O I：

10.1016/j.tetasy.2015.10.022

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Simple chiral triethylsilyl-amino alcohol organocatalysts containing a bulky triethylsilyl group on the oxygen atom at the gamma-position were designed and synthesized as new organocatalysts for enantioselective Diels-Alder reactions of anthrones with maleimides to produce chiral hydroanthracene Diels-Alder adducts in up to 99% yield and with up to 94% ee. (c) 2015 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1423 / 1429

页数：7

相关论文

共 20 条

[1] A first case of asymmetric catalysis induced by metal-free bisoxazolines [J].

Akalay, Deniz ;

Duerner, Gerd ;

Goebel, Michael W. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (14) :2365-2368

[2] Enantioselective addition of anthrones to α,β-unsaturated aldehydes [J].

Alba, Andrea-Nekane ;

Bravo, Natalia ;

Moyano, Albert ;

Rios, Ramon .

TETRAHEDRON LETTERS, 2009, 50 (25) :3067-3069

[3] Enantioselective Diels-Alder reaction of anthrone and maleimide catalyzed by a simple chiral tertiary amine [J].

Bai, Jian-Fei ;

Guo, Yun-Long ;

Peng, Lin ;

Jia, Li-Na ;

Xu, Xiao-Ying ;

Wang, Li-Xin .

TETRAHEDRON, 2013, 69 (03) :1229-1233

[4] A new chiral anthracene for the asvmmetric Diels-Alder/retro-Diels-Alder sequence [J].

Burgess, KL ;

Lajkiewicz, NJ ;

Sanyal, A ;

Yan, WL ;

Snyder, JK .

ORGANIC LETTERS, 2005, 7 (01) :31-34

[5] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[6] New perfluoroalkylated cinchona derivatives: synthesis and use in base-catalysed Diels-Alder reactions [J].

Fache, F ;

Piva, O .

TETRAHEDRON LETTERS, 2001, 42 (33) :5655-5657

[7] Enantioselective Die Is Alder Reaction of 1,2-Dihydropyridines with Aldehydes Using β-Amino Alcohol Organocatalyst [J].

Kohari, Yoshihito ;

Okuyama, Yuko ;

Kwon, Eunsang ;

Furuyama, Taniyuki ;

Kobayashi, Nagao ;

Otuki, Teppei ;

Kumagai, Jun ;

Seki, Chigusa ;

Uwai, Koji ;

Dai, Gang ;

Iwasa, Tatsuo ;

Nakano, Hiroto .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (20) :9500-9511

[8] Asymmetric aminocatalysis [J].

List, B .

SYNLETT, 2001, (11) :1675-1686

[9] Microwave-assisted synthesis and structure-activity relationships of neuroactive pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine derivatives [J].

Nascimento-Junior, Nailton M. ;

Mendes, Thaiana C. F. ;

Leal, Daniella M. ;

Correa, Claudia Maria N. ;

Sudo, Roberto T. ;

Zapata-Sudo, Gisele ;

Barreiro, Eliezer J. ;

Fraga, Carlos A. M. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (01) :74-77

[10] Rigidized 1-aryl sulfonyl tryptamines: Synthesis and pharmacological evaluation as 5-HT6 receptor ligands [J].

Nirogi, Ramakrishna ;

Dwarampudi, Adireddy ;

Kambhampati, Ramasastry ;

Bhatta, Venugopalarao ;

Kota, Laxman ;

Shinde, Anil ;

Badange, Rajesh ;

Jayarajan, Pradeep ;

Bhyrapuneni, Gopinadh ;

Dubey, P. K. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (15) :4577-4580