Müller, T. J. J.: 2014 Science of Synthesis, 2013/6: Multicomponent Reactions, Volume 2 DOI: 10.1055/sos-SD-211-00046
Multicomponent Reactions, Volume 2

2.1.7 [4 + 2] Cycloaddition as the Key Step

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Book

Editor: Müller, T. J. J.

Authors: Alavijeh, N. S.; Arndtsen, B. A.; Balalaie, S.; Bonne, D.; Chen, C.; Coquerel, Y.; Elliott, M.; Festa, A.; Fusano, A.; Ghabraie, E.; Jones, D. H.; Modha, S.; Müller, T. J. J.; Purushothaman, S.; Raghunathan, R.; Rodriguez, J.-A.; Ryu, I.; Sarvary, A.; Shaabani, A.; Shaabani, S.; Szabó, K. J.; Takasu, K.; Tjutrins, J.; Van der Eycken, E.; Voskressensky, L.; Wan, J.; Xi, C.

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

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.

 
  • 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
  • 15 Ikoma M, Oikawa M, Sasaki M. Eur. J. Org. Chem. 2009; 72
  • 18 Medimagh R, Marque S, Prim D, Chatti S. Synthesis 2010; 770
  • 19 Zamudio-Medina A, García-González MC, Padilla J, González-Zamora E. Tetrahedron Lett. 2010; 51: 4837
  • 28 Mukherjee S, Roy P, Ghorai BK. Synthesis 2011; 1419
  • 29 Jana GP, Mukherjee S, Ghorai BK. Synthesis 2010; 3179
  • 30 Oppolzer W, Bieber L, Francotte E. Tetrahedron Lett. 1979; 4537
  • 31 Hübner S, Neumann H, Jacobi von Wangelin A, Klaus S, Strübing D, Klein H, Beller M. Synthesis 2005; 2084
  • 34 Neumann H, Jacobi von Wangelin A, Gördes D, Spannenberg A, Baumann W, Beller M. Tetrahedron 2002; 58: 2381
  • 36 Virolleaud M.-A, Piva O. Eur. J. Org. Chem. 2007; 1606
  • 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
  • 51 Simon C, Constantieux T, Rodriguez J. Eur. J. Org. Chem. 2004; 4957
  • 53 Tietze LF, Meier H, Nutt H. Liebigs Ann. Chem. 1990; 253
  • 54 Tietze LF, Meier H, Nutt H. Chem. Ber. 1989; 643
  • 56 Tietze LF, Hippe T, Steinmetz A. Synlett 1996; 1043
  • 57 Li L, Wu Q, Liu B.-K, Lin X.-F. Synthesis 2011; 563
  • 58 Erver F, Hilt G, Harms K. Synthesis 2011; 972
  • 59 Tietze LF, Dietz S, Böhnke N, Düfert MA, Objartel I, Stalke D. Eur. J. Org. Chem. 2011; 6574
  • 62 Palasz A. Synthesis 2010; 4021
  • 66 Appendino G, Cravotto G, Minassi A, Palmisano G. Eur. J. Org. Chem. 2001; 3711
  • 67 Bharate SB, Mudududdla R, Bharate JB, Battini N, Battula S, Yadav RR, Singh B, Vishwakarma RA. Org. Biomol. Chem. 2012; 10: 5143
  • 68 Dediu OG, Yehia NAM, Oeser T, Polborn K, Müller TJJ. Eur. J. Org. Chem. 2005; 1834
  • 72 Ramachary DB, Chowdari NS, Barbas III CF. Synlett 2003; 1910