Enantioselective Synthesis of Bicyclic δ-Lactones via N-Heterocyclic Carbene-Catalyzed Cascade Reaction

被引：54

作者：

Liang, Zhi-Qin ^{[1
]}

Wang, Dong-Ling ^{[1
]}

Zhang, Han-Ming ^{[1
]}

Ye, Song ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 20期

基金：

美国国家科学基金会;

关键词：

DIELS-ALDER REACTIONS; HIGHLY STEREOSELECTIVE-SYNTHESIS; INTERMOLECULAR STETTER REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; ASYMMETRIC-SYNTHESIS; BENZOIN REACTIONS; 4+2 ANNULATION; COOPERATIVE CATALYSIS; GAMMA-BUTYROLACTONES; ALIPHATIC-ALDEHYDES;

D O I：

10.1021/acs.orglett.5b02695

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The N-heterocyclic carbene-catalyzed cascade reaction of enals with malonates to give bicyclic delta-lactones was developed. The cyclopentane- and cyclohexane-fused delta-lactones with three continued stereocenters were obtained in high yields with excellent diastereo- and high enantioselectivities.

引用

页码：5140 / 5143

页数：4

共 80 条

[1] Asymmetric Synthesis of Highly Substituted β-Lactones through Oxidative Carbene Catalysis with LiCl as Cooperative Lewis Acid [J].

Bera, Srikrishna ;

Samanta, Ramesh C. ;

Daniliuc, Constantin G. ;

Studer, Armido .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9622-9626

[2] 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

[3] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].

Burstein, C ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208

[4] Enantioselective All-Carbon (4+2) Annulation by N-Heterocyclic Carbene Catalysis [J].

Candish, Lisa ;

Levens, Alison ;

Lupton, David W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (41) :14397-14400

[5] N-Heterocyclic Carbene-Catalyzed Ireland-Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones [J].

Candish, Lisa ;

Lupton, David W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (01) :58-61

[6] 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

[7] 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-+

[8] Direct amination of homoenolates catalyzed by N-Heterocyclic carbenes [J].

Chan, Audrey ;

Scheidt, Karl A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) :2740-+

[9] 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

[10] Highly Enantioselective γ-Amination by N-Heterocyclic Carbene Catalyzed [4+2] Annulation of Oxidized Enals and Azodicarboxylates [J].

Chen, Xiang-Yu ;

Xia, Fei ;

Cheng, Jin-Tang ;

Ye, Song .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (40) :10644-10647

← 1 2 3 4 5 6 7 8 →