N-Heterocyclic Carbene-Catalyzed Ireland-Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones

被引：144
作者：
Candish, Lisa [1 ]
Lupton, David W. [1 ]
机构：
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 01期
关键词：
ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE SYNTHESIS; ENALS; ANNULATIONS; (-)-7-DEOXYLOGANIN; TRIAZOLIUM; SALT;
D O I：
10.1021/ja310449k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The N-heterocyclic carbene (NHC)-catalyzed Claisen rearrangement of hybrid Ireland-Coates structures has been achieved, allowing the stereoselective synthesis of highly functionalized beta-lactones. The reaction proceeds with high diastereoselectivity (>20:1) and affords a diverse range of beta-lactone fused cyclopentanes. Mechanistic studies are detailed.
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页码：58 / 61
页数：4
相关论文
共 57 条
[1]  
Abraham L, 2001, ANGEW CHEM INT EDIT, V40, P4700, DOI 10.1002/1521-3773(20011217)40:24<4700::AID-ANIE4700>3.0.CO
[2]  
2-6
[3]   Enantioselective cyclopropanation of enals by oxidative N-heterocyclic carbene catalysis [J].
Biswas, Anup ;
De Sarkar, Suman ;
Tebben, Ludger ;
Studer, Armido .
CHEMICAL COMMUNICATIONS, 2012, 48 (42) :5190-5192
[4]   Highly Stereoselective Synthesis of 1,2,3-Trisubstituted Indanes via Oxidative N-Heterocyclic Carbene-Catalyzed Cascades [J].
Biswas, Anup ;
De Sarkar, Suman ;
Froehlich, Roland ;
Studer, Armido .
ORGANIC LETTERS, 2011, 13 (18) :4966-4969
[5]   N-heterocyclic carbene-catalyzed redox amidations of α-functionalized aldehydes with amines [J].
Bode, Jeffrey W. ;
Sohn, Stephanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13798-+
[6]   N-heterocyclic carbene-catalyzed conjugate umpolung for the synthesis of γ-butyrolactones [J].
Burstein, Christian ;
Tschan, Serena ;
Xie, Xiulan ;
Glorius, Frank .
SYNTHESIS-STUTTGART, 2006, (14) :2418-2439
[7]   N-heterocyclic carbene cascade catalysis: Dual Bronsted/Lewis base rearrangement of cyclopropyl enol esters to dihydropyranones [J].
Candish, Lisa ;
Lupton, David W. .
CHEMICAL SCIENCE, 2012, 3 (02) :380-383
[8]   Concise formal synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters [J].
Candish, Lisa ;
Lupton, David W. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (23) :8182-8189
[9]   The Total Synthesis of (-)-7-Deoxyloganin via N-Heterocyclic Carbene Catalyzed Rearrangement of α,β-Unsaturated Enol Esters [J].
Candish, Lisa ;
Lupton, David W. .
ORGANIC LETTERS, 2010, 12 (21) :4836-4839
[10]   Claisen rearrangement over the past nine decades [J].
Castro, AMM .
CHEMICAL REVIEWS, 2004, 104 (06) :2939-3002
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