Asymmetric Inverse-Electron-Demand Diels-Alder Reactions of 2-Pyrones by Lewis Acid Catalysis

被引：11

作者：

Si, Xu-Ge ^{[1
]}

Zhang, Zhi-Mao ^{[1
]}

Cai, Quan ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China

来源：

SYNLETT | 2021年 / 32卷 / 10期

基金：

中国国家自然科学基金;

关键词：

pyrones; asymmetric catalysis; Diels-Alder reactions; Lewis acid catalysis; natural product synthesis; CROTONIN; NORDITERPENE;

D O I：

10.1055/a-1371-4391

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diels-Alder reactions of 2-pyrones with alkenes can provide highly functionalized [2,2,2]-bicyclic lactones under mild reaction conditions. Synthetic utilizations of these reactions have been well demonstrated in natural-product synthesis. Although several catalytic asymmetric strategies have been realized, current research in this area is still largely underdeveloped. Recent advances in enantioselective inverse-electron-demand Diels-Alder reactions with Lewis acid catalysis are reviewed. 1 Introduction 2 State of the Art of Enantioselective Diels-Alder Reactions of 2-Pyrones by Lewis Acid Catalysis 3 Enantioselective Synthesis of Arene cis-Dihydrodiols by DielsAlder/Retro-Diels-Alder Reactions of 2-Pyrones 4 Enantioselective Synthesis of cis-Decalin Derivatives by DielsAlder Reactions of 2-Pyrones 5 Conclusions

引用

页码：947 / 954

页数：8

共 84 条

[1] DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES [J].

AFARINKIA, K ;

VINADER, V ;

NELSON, TD ;

POSNER, GH .

TETRAHEDRON, 1992, 48 (42) :9111-9171

[2] Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin [J].

Baidilov, Daler ;

Rycek, Lukas ;

Trant, John F. ;

Froese, Jordan ;

Murphy, Brennan ;

Hudlicky, Tomas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (34) :10994-10998

[3] A BIOTECH ROUTE TO POLYPHENYLENE [J].

BALLARD, DGH ;

COURTIS, A ;

SHIRLEY, IM ;

TAYLOR, SC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) :954-955

[4] Catalytic asymmetric [4+2] additions with aliphatic nitroalkenes [J].

Bartelson, Keith J. ;

Singh, Ravi P. ;

Foxman, Bruce M. ;

Deng, Li .

CHEMICAL SCIENCE, 2011, 2 (10) :1940-1944

[5] Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene [J].

Bingham, Tanner W. ;

Hernandez, Lucas W. ;

Olson, Daniel G. ;

Svec, Riley L. ;

Hergenrother, Paul J. ;

Sarlah, David .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (01) :657-670

[6]

BLOUNT JF, 1984, J CHEM RES, P114

[7]

Boyd DR, 1998, NAT PROD REP, V15, P309

[8] Total Synthesis of Gelsemiol [J].

Burch, Patrick ;

Binaghi, Massimo ;

Scherer, Manuel ;

Wentzel, Corinna ;

Bossert, David ;

Eberhardt, Luc ;

Neuburger, Markus ;

Scheiffele, Peter ;

Gademann, Karl .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (08) :2589-2591

[9] The [4+2] Cycloaddition of 2-Pyrone in Total Synthesis [J].

Cai, Quan .

CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (09) :946-976

[10] Catalytic asymmetric arylation of aliphatic aldehydes using a B/Zn exchange reaction [J].

Carlos, Andressa M. M. ;

Contreira, Maria Eduarda ;

Martins, Bruna S. ;

Immich, Maira F. ;

Moro, Angelica V. ;

Luedtke, Diogo S. .

TETRAHEDRON, 2015, 71 (08) :1202-1206

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