2.1. 7 [4 + 2] Cycloaddition as the Key Step
Book
Editor: Müller, T. J. J.
Title: Multicomponent Reactions, Volume 2
Subtitle: Reactions Involving an α,α-Unsaturated Carbonyl Compound as Electrophilic Component, Cycloadditions, and Boron-, Silicon-, Free-Radical-, and Metal-Mediated Reactions
Print ISBN: 9783131728319; Online ISBN: 9783132064317; Book DOI: 10.1055/b-003-125831
1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Multicomponent Reactions
Science of Synthesis Reference Libraries
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract
α, β-Unsaturated carbonyl compounds are widely used as dienes and as dienophiles in [4 + 2] cycloadditions. This review covers those cycloaddition reactions in which a multicomponent reaction is used either in the formation of the α, β-unsaturated carbonyl compound or for the assembly of the final product. The review is organized according to the role of the carbonyl component (diene or dienophile) and whether it is introduced as a reagent or formed during the reaction.
Key words
alkenation - asymmetric synthesis - [4 + 2] cycloaddition - cyclohexenes - Diels–Alder reaction - diketones - enals - enones - isoindoles - Knoevenagel condensation - oxazoles - pyridines- 4 Le Coz L, Veyrat-Martin C, Wartsky L, Seyden-Penne J, Bois C, Philoche-Levisalles M. J. Org. Chem. 1990; 55: 4870
- 5 Costantino U, Fringuelli F, Orru M, Nocchetti M, Piermatti O, Pizzo F. Eur. J. Org. Chem. 2009; 1214
- 6 Borkin D, Morzhina E, Datta S, Rudnitskaya A, Sood A, Török M, Török B. Org. Biomol. Chem. 2011; 9: 1394
- 19 Zamudio-Medina A, García-González MC, Padilla J, González-Zamora E. Tetrahedron Lett. 2010; 51: 4837
- 31 Hübner S, Neumann H, Jacobi von Wangelin A, Klaus S, Strübing D, Klein H, Beller M. Synthesis 2005; 2084
- 32 Jacobi von Wangelin A, Neumann H, Gördes D, Klaus S, Strübing D, Beller M. Chem.–Eur. J. 2003; 9: 4286
- 33 Neumann H, Jacobi von Wangelin A, Gördes D, Spannenberg A, Beller M. J. Am. Chem. Soc. 2001; 123: 8398
- 34 Neumann H, Jacobi von Wangelin A, Gördes D, Spannenberg A, Baumann W, Beller M. Tetrahedron 2002; 58: 2381
- 38 Komagawa S, Takeuchi K, Sotome I, Azumaya I, Masu H, Yamasaki R, Saito S. J. Org. Chem. 2009; 74: 3323
- 40 de Meijere A, Nüske H, Es-Sayed M, Labahn T, Schroen T, Bräse S. Angew. Chem. Int. Ed. 1999; 38: 3669
- 42 Klaus S, Hübner S, Neumann H, Strübing D, Jacobi von Wangelin A, Gördes D, Beller M. Adv. Synth. Catal. 2004; 346: 970
- 44 Strübing D, Neumann H, Jacobi von Wangelin A, Klaus S, Hübner S, Beller M. Tetrahedron 2006; 62: 10962
- 45 Strübing D, Jacobi von Wangelin A, Neumann H, Gördes D, Hübner S, Klaus S, Spannenberg A, Beller M. Eur. J. Org. Chem. 2005; 107
- 46 Hübner S, Jiao H, Michalik D, Neumann H, Klaus S, Strübing D, Spannenberg A, Beller M. Chem.–Asian J. 2007; 2: 720
- 48 Hübner S, Michalik D, Jiao H, Neumann H, Klaus S, Strübing D, Spannenberg A, Beller M. Chem.–Asian J. 2007; 2: 734