N-heterocyclic carbene-catalyzed cyclocondensation of 2-aryl carboxylic acids and enones: highly enantioselective synthesis of δ-lactones

被引:23
作者
Cheng, Jin-Tang [1 ]
Chen, Xiang-Yu [1 ]
Ye, Song [1 ,2 ]
机构
[1] Chinese Acad Sci, Key Lab Mol Recognit & Funct, Inst Chem, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[2] Jiangxi Normal Univ, Natl Engn Res Ctr Carbohydrate Synth, Nanchang 330022, Peoples R China
基金
美国国家科学基金会;
关键词
DIELS-ALDER REACTIONS; TRICYCLIC-BETA-LACTONES; ASYMMETRIC-SYNTHESIS; TRIFLUOROMETHYL DIHYDROPYRANONES; DISUBSTITUTED KETENES; ENOLATE EQUIVALENTS; ALDOL-LACTONIZATION; 4+2 CYCLOADDITION; KETO ACIDS; DERIVATIVES;
D O I
10.1039/c4ob02330g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective N-heterocyclic carbene-catalyzed [4 + 2] cyclocondensation of 2-aryl carboxylic acids and enones was developed, affording the corresponding chiral delta-lactones in good yields with good diastereo- and high enantioselectivities.
引用
收藏
页码:1313 / 1316
页数:4
相关论文
共 68 条
[1]   Palladium-Catalyzed β-Arylation of Silyl Ketene Acetals and Application to the Synthesis of Benzo-Fused δ-Lactones [J].
Aspin, Sam ;
Lopez-Suarez, Laura ;
Larini, Paolo ;
Goutierre, Anne-Sophie ;
Jazzar, Rodolphe ;
Baudoin, Olivier .
ORGANIC LETTERS, 2013, 15 (19) :5056-5059
[2]   Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations [J].
Belmessieri, Dorine ;
Morrill, Louis C. ;
Simal, Carmen ;
Slawin, Alexandra M. Z. ;
Smith, Andrew D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (08) :2714-2720
[3]   CARBENE CATALYSIS An internal affair [J].
Bode, Jeffrey W. .
NATURE CHEMISTRY, 2013, 5 (10) :813-815
[4]   Synthetic approaches to α,β-unsaturated δ-lactones and lactols [J].
Boucard, Valerie ;
Broustal, Garance ;
Campagne, Jean Marc .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (02) :225-236
[5]   Organocatalytic umpolung: N-heterocyclic carbenes and beyond [J].
Bugaut, Xavier ;
Glorius, Frank .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3511-3522
[6]   Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates [J].
Cardinal-David, Benoit ;
Raup, Dustin E. A. ;
Scheidt, Karl A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) :5345-+
[7]   Asymmetric Access to the Smallest Enolate Intermediate via Organocatalytic Activation of Acetic Ester [J].
Chen, Shaojin ;
Hao, Lin ;
Zhang, Yuexia ;
Tiwari, Bhoopendra ;
Chi, Yonggui Robin .
ORGANIC LETTERS, 2013, 15 (22) :5822-5825
[8]   N-Heterocyclic Carbene Catalyzed Cyclocondensation of α,β-Unsaturated Carboxylic Acids: Enantioselective Synthesis of Pyrrolidinone and Dihydropyridinone Derivatives [J].
Chen, Xiang-Yu ;
Gao, Zhong-Hua ;
Song, Chun-Yu ;
Zhang, Chun-Lin ;
Wang, Zhi-Xiang ;
Ye, Song .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (43) :11611-11615
[9]   Intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL) reactions:: Catalytic, asymmetric synthesis of bicyclic β-lactones [J].
Cortez, GS ;
Tennyson, RL ;
Romo, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) :7945-7946
[10]   Asymmetric Synthesis of Tri- and Tetrasubstituted Trifluoromethyl Dihydropyranones from α-Aroyloxyaldehydes via NHC Redox Catalysis [J].
Davies, Alyn T. ;
Pickett, Philip M. ;
Slawin, Alexandra M. Z. ;
Smith, Andrew D. .
ACS CATALYSIS, 2014, 4 (08) :2696-2700