Highly enantioselective direct vinylogous Michael addition of γ-substituted deconjugated butenolides to maleimides catalyzed by chiral squaramides

被引：37

作者：

Guo, Yun-Long ^{[1
,2
]}

Jia, Li-Na ^{[1
,2
]}

Peng, Lin ^{[1
]}

Qi, Liang-Wen ^{[1
,2
]}

Zhou, Jing ^{[1
,2
]}

Tian, Fang ^{[1
]}

Xu, Xiao-Ying ^{[1
]}

Wang, Li-Xin ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 10039, Peoples R China

来源：

RSC ADVANCES | 2013年 / 3卷 / 38期

基金：

中国国家自然科学基金;

关键词：

1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITION; 3+2 ANNULATION; CONSTRUCTION; CARBONATES;

D O I：

10.1039/c3ra43344g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly enantioselective direct vinylogous Michael reactions of gamma-aryl-substituted deconjugated butenolides with maleimides, catalyzed by only 1 mol% bifunctional squaramides derived from cinchona alkaloids, were achieved with excellent yields (up to 96%) and enantioselectivities (up to 97% ee). This protocol features a very low catalyst loading, mild reaction conditions and provides a potential and effective method for the construction of optically active chiral butenolides with adjacent quaternary and tertiary stereocenters.

引用

页码：16973 / 16976

页数：4

共 57 条

[1] Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis [J].

Aleman, Jose ;

Parra, Alejandro ;

Jiang, Hao ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) :6890-6899

[2] Organocatalytic asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides [J].

Bartoli, Giuseppe ;

Bosco, Marcella ;

Carlone, Armando ;

Cavalli, Andrea ;

Locatelli, Manuela ;

Mazzanti, Andrea ;

Ricci, Paolo ;

Sambri, Letizia ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (30) :4966-4970

[3] Azaphilones from the Endophyte Chaetomium globosum [J].

Borges, Warley S. ;

Mancila, Gabriela ;

Guimaraes, Denise O. ;

Duran-Patron, Rosa ;

Collado, Isidro G. ;

Pupo, Monica T. .

JOURNAL OF NATURAL PRODUCTS, 2011, 74 (05) :1182-1187

[4] The first enantioselective organocatalytic Mukaiyama- Michael reaction:: A direct method for the synthesis of enantioenriched γ-butenolide architecture [J].

Brown, SP ;

Goodwin, NC ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1192-1194

[5] Asymmetric Organocatalytic Addition Reactions of Maleimides: A Promising Approach Towards the Synthesis of Chiral Succinimide Derivatives [J].

Chauhan, Pankaj ;

Kaur, Jasneet ;

Chimni, Swapandeep Singh .

CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (02) :328-346

[6]

Christoffers, 2001, ANGEW CHEM, V113, P4725

[7]

Christoffers J, 2005, QUATERNARY STEREOCENTERS: CHALLENGES AND SOLUTIONS FOR ORGANIC SYNTHESIS, P1, DOI 10.1002/3527606858

[8]

Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO

[9]

2-V

[10] A Catalytic Asymmetric Reaction Involving Enolizable Anhydrides [J].

Cornaggia, Claudio ;

Manoni, Francesco ;

Torrente, Esther ;

Tallon, Sean ;

Connon, Stephen J. .

ORGANIC LETTERS, 2012, 14 (07) :1850-1853

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