Müller, T. J. J.: 2014 Science of Synthesis, 2013/6: Multicomponent Reactions, Volume 2 DOI: 10.1055/sos-SD-211-00002
Multicomponent Reactions, Volume 2

2.1 Reactions Involving an α,β-Unsaturated Carbonyl Compound or Analogue as Electrophilic Component

More Information

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

This chapter focuses on multicomponent reactions involving an α, β-unsaturated compound as an electrophilic component and in which a Michael addition is a key step during the process. The Michael addition step can be either the starting point or a late event in the domino sequence. These reactions are extremely powerful processes, allowing the synthesis of diverse, valuable carbocyclic, heterocyclic, or acyclic scaffolds.

 
  • 1 Tokoroyama T. Eur. J. Org. Chem. 2010; 2009
  • 2 Liéby-Muller F, Simon C, Constantieux T, Rodriguez J. QSAR Comb. Sci. 2006; 25: 432
  • 3 Sanchez del Duque M, Allais C, Isambert N, Constantieux T, Rodriguez J. Top. Heterocycl. Chem. 2010; 23: 227
  • 4 Lavilla R. J. Chem. Soc., Perkin Trans. 1 2002; 1141
  • 5 Bello D, Ramón R, Lavilla R. Curr. Org. Chem. 2010; 14: 332
  • 6 Maiti S, Sridharan V, Menéndez JC. J. Comb. Chem. 2010; 12: 713
  • 7 Michael JP. Nat. Prod. Rep. 2005; 22: 627
  • 8 Liéby-Muller F, Allais C, Constantieux T, Rodriguez J. Chem. Commun. (Cambridge) 2008; 4207
  • 9 Allais C, Constantieux T, Rodriguez J. Chem.–Eur. J. 2009; 15: 12945
  • 10 Sundberg RJ. The Chemistry of Indoles. Academic; New York 1996
  • 11 Sun J, Sun Y, Gao H, Yan C.-G. Eur. J. Org. Chem. 2012; 1976
  • 12 Walsh CT, Gameau-Tsodikova S, Howard-Jones AR. Nat. Prod. Rep. 2006; 23: 517
  • 13 Hantzsch A. Ber. Dtsch. Chem. Ges. 1890; 23: 1474
  • 14 Das B, Bhunia N, Lingaiah M. Synthesis 2011; 3471
  • 15 Habib-Zahmani H, Hacini S, Bories C, Faure R, Rodriguez J. Synthesis 2005; 2151
  • 16 Wang D.-W, Syu S, Hung Y.-T, Chen P, Lee C.-J, Chen K.-W, Chen Y.-J, Lin W. Org. Biomol. Chem. 2011; 9: 363
  • 17 Peña D, Pérez D, Guitián E. Angew. Chem. Int. Ed. 2006; 45: 3579
  • 18 Bhojgude SD, Biju AT. Angew. Chem. Int. Ed. 2012; 51: 1520
  • 19 Huang X, Xue J. J. Org. Chem. 2007; 72: 3965
  • 20 Alizadeh A, Rezvanian A, Mokhtari J. Synthesis 2011; 3491
  • 21 Shibuya M, Jaisli F, Eschenmoser A. Angew. Chem. Int. Ed. Engl. 1979; 18: 636
  • 22 Simon C, Peyronel J.-F, Rodriguez J. Org. Lett. 2001; 3: 2145
  • 23 Liéby-Muller F, Constantieux T, Rodriguez J. Synlett 2007; 1323
  • 24 Noël R, Fargeau-Bellassoued M.-C, Vanucci-Bacqué C, Lhommet G. Synthesis 2008; 1948
  • 25 Simon C, Liéby-Muller F, Peyronel J.-F, Constantieux T, Rodriguez J. Synlett 2003; 2301
  • 26 Sridharan V, Menéndez JC. Org. Lett. 2008; 10: 4303
  • 27 Sridharan V, Maiti S, Menéndez JC. Chem.–Eur. J. 2009; 15: 4565
  • 28 Liéby-Muller F, Constantieux T, Rodriguez J. J. Am. Chem. Soc. 2005; 127: 17176
  • 29 Filippini M.-H, Faure R, Rodriguez J. J. Org. Chem. 1995; 60: 6872
  • 30 Coquerel Y, Filippini M.-H, Bensa D, Rodriguez J. Chem.–Eur. J. 2008; 14: 3078
  • 31 Reboul I, Boddaert T, Coquerel Y, Rodriguez J. Eur. J. Org. Chem. 2008; 5379
  • 32 Boddaert T, Coquerel Y, Rodriguez J. Chem.–Eur. J. 2011; 17: 2048
  • 33 Coquerel Y, Bensa D, Moret V, Rodriguez J. Synlett 2006; 2751
  • 34 Coquerel Y, Bensa D, Doutheau A, Rodriguez J. Org. Lett. 2006; 8: 4819
  • 35 Zhang B, Cai L, Song H, Wang Z, He Z. Adv. Synth. Catal. 2010; 352: 97
  • 36 Wei J, Shaw JT. Org. Lett. 2007; 9: 4077
  • 37 Xu Z, Buechler T, Wheeler K, Wang H. Chem.–Eur. J. 2010; 16: 2972
  • 38 de Graaff C, Ruijter E, Orru RVA. Chem. Soc. Rev. 2012; 41: 3969
  • 39 Enders D, Hüttl MRM, Grondal C, Raabe G. Nature (London) 2006; 441: 861
  • 40 Enders D, Hüttl MRM, Runsink J, Raabe G, Wendt B. Angew. Chem. Int. Ed. 2007; 46: 467
  • 41 Enders D, Hüttl MRM, Raabe G, Bats JW. Adv. Synth. Catal. 2008; 350: 267
  • 42 Wang Y, Han R.-G, Zhao Y.-L, Yang S, Xu P.-F, Dixon DJ. Angew. Chem. Int. Ed. 2009; 48: 9834
  • 43 Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
  • 44 Lo MM.-C, Neumann CS, Nagayama S, Perlstein EO, Schreiber SL. J. Am. Chem. Soc. 2004; 126: 16077
  • 45 Bencivenni G, Wu L.-Y, Mazzanti A, Giannichi B, Pesciaioli F, Song M.-P, Bartoli G, Melchiorre P. Angew. Chem. Int. Ed. 2009; 48: 7200
  • 46 Jiang K, Jia Z.-J, Chen S, Wu L, Chen Y.-C. Chem.–Eur. J. 2010; 16: 2852
  • 47 Coquerel Y, Boddaert T, Presset M, Mailhol D, Rodriguez J, Ideas in Chemistry and Molecular Sciences: Advances in Synthetic Chemistry. Pignataro B. Wiley-VCH; Weinheim, Germany 2010
  • 48 Jiang K, Jia Z.-J, Yin X, Wu L, Chen Y.-C. Org. Lett. 2010; 12: 2766
  • 49 Cassani C, Tian X, Escudero-Adán EC, Melchiorre P. Chem. Commun. (Cambridge) 2011; 47: 233
  • 50 Zea A, Alba A.-NR, Mazzanti A, Moyano A, Rios R. Org. Biomol. Chem. 2011; 9: 6519
  • 51 Huang Y, Walji AM, Larsen CH, MacMillan DWC. J. Am. Chem. Soc. 2005; 127: 15051
  • 52 Simmons B, Walji AM, MacMillan DWC. Angew. Chem. Int. Ed. 2009; 48: 4349
  • 53 Zhang F.-L, Xu A.-W, Gong Y.-F, Wei M.-H, Yang X.-L. Chem.–Eur. J. 2009; 15: 6815
  • 54 Kotame P, Hong B.-C, Liao J.-H. Tetrahedron Lett. 2009; 50: 704
  • 55 Hong B.-C, Kotame P, Tsai C.-W, Liao J.-H. Org. Lett. 2010; 12: 776
  • 56 Maiti S, Menéndez JC. Synlett 2009; 2249
  • 57 Jiang J, Yu J, Sun X.-X, Rao Q.-Q, Gong L.-Z. Angew. Chem. Int. Ed. 2008; 47: 2458
  • 58 Yu J, Shi F, Gong L.-Z. Acc. Chem. Res. 2011; 44: 1156
  • 59 Jiang J, Qing J, Gong L.-Z. Chem.–Eur. J. 2009; 15: 7031
  • 60 Franke PT, Johansen RL, Bertelsen S, Jørgensen KA. Chem.–Asian J. 2008; 3: 216
  • 61 Fraile A, Scarpino Schietroma DM, Albrecht A, Davis RL, Jørgensen KA. Chem.–Eur. J. 2012; 18: 2773