PDF herunterladen
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

Weitere Informationen

Buch

Herausgeber: Müller, T. J. J.

Autoren: 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.

Titel: Multicomponent Reactions, Volume 2

Untertitel: 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; Buch-DOI: 10.1055/b-003-125831

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: Multikomponenten-Reaktionen

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Typ: Mehrbändiges Werk

Auch verfügbar auf
 


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.

Schlüsselwörter

alkenation - asymmetric synthesis - [4 + 2] cycloaddition - cyclohexenes - Diels–Alder reaction - diketones - enals - enones - isoindoles - Knoevenagel condensation - oxazoles - pyridines
 
  • 1 Posner GH. Chem. Rev. 1986; 86: 831
  • 2 Isambert N, Lavilla R. Chem.–Eur. J. 2008; 14: 8444
    PubMed
  • 3 Lin C, Fang H, Tu Z, Liu J.-T, Yao C.-F. J. Org. Chem. 2006; 71: 6588
    PubMed
  • 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
    PubMed
  • 7 Kouznetsov VV. Tetrahedron 2009; 65: 2721
  • 8 Kudale AA, Kendall J, Miller DO, Collins JL, Bodwell GJ. J. Org. Chem. 2008; 73: 8437
    PubMed
  • 9 Guillena G, Ramón DJ, Yus M. Tetrahedron: Asymmetry 2007; 18: 693
  • 10 Enders D, Grondal C, Hüttl MRM. Angew. Chem. Int. Ed. 2007; 46: 1570
    PubMed
  • 11 Notz W, Takana F, Barbas III CF. Acc. Chem. Res. 2004; 37: 580
    PubMed
  • 12 Enders D, Hüttl MRM, Runsink J, Raabe G, Wendt B. Angew. Chem. Int. Ed. 2007; 46: 467
    PubMed
  • 13 Paulvannan K. Tetrahedron Lett. 1999; 40: 1851
  • 14 Paulvannan K. J. Org. Chem. 2004; 69: 1207
    PubMed
  • 15 Ikoma M, Oikawa M, Sasaki M. Eur. J. Org. Chem. 2009; 72
  • 16 Yin Y, Zhao G, Li G.-L. Tetrahedron 2005; 61: 12042
  • 17 Santra S, Andreana PR. Org. Lett. 2007; 9: 5035
    PubMed
  • 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
  • 20 Islas-Jácome A, González-Zamora E, Gámez-Montaño R. Tetrahedron Lett. 2011; 52: 5245
  • 21 Lalli C, Bouma MJ, Bonne D, Masson G, Zhu J. Chem.–Eur. J. 2011; 17: 880
    PubMed
  • 22 Zhang L, Malinakova HC. J. Org. Chem. 2007; 72: 1484
    PubMed
  • 23 Sunderhaus JD, Dockendorff C, Martin SF. Org. Lett. 2007; 9: 4223
    PubMed
  • 24 Wang X.-S, Zhou J, Yang K, Yao C.-S. Tetrahedron Lett. 2010; 51: 5721
  • 25 Chen C.-H, Yellol GS, Lin P.-T, Sun C.-M. Org. Lett. 2011; 13: 5120
    PubMed
  • 26 Duan S, Sinha-Mahapatra DK, Herndon JW. Org. Lett. 2008; 10: 1541
    PubMed
  • 27 Roy P, Ghorai BK. Beilstein J. Org. Chem. 2010; 6: 52
    PubMed
  • 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
  • 32 Jacobi von Wangelin A, Neumann H, Gördes D, Klaus S, Strübing D, Beller M. Chem.–Eur. J. 2003; 9: 4286
    PubMed
  • 33 Neumann H, Jacobi von Wangelin A, Gördes D, Spannenberg A, Beller M. J. Am. Chem. Soc. 2001; 123: 8398
    PubMed
  • 34 Neumann H, Jacobi von Wangelin A, Gördes D, Spannenberg A, Baumann W, Beller M. Tetrahedron 2002; 58: 2381
  • 35 Lee H.-Y, Kim HY, Tae H, Kim BG, Lee J. Org. Lett. 2003; 5: 3439
    PubMed
  • 36 Virolleaud M.-A, Piva O. Eur. J. Org. Chem. 2007; 1606
  • 37 Yamamoto Y, Hayashi H. Tetrahedron 2007; 63: 10149
  • 38 Komagawa S, Takeuchi K, Sotome I, Azumaya I, Masu H, Yamasaki R, Saito S. J. Org. Chem. 2009; 74: 3323
    PubMed
  • 39 Lee PH, Lee K, Kang Y. J. Am. Chem. Soc. 2006; 128: 1139
    PubMed
  • 40 de Meijere A, Nüske H, Es-Sayed M, Labahn T, Schroen T, Bräse S. Angew. Chem. Int. Ed. 1999; 38: 3669
    PubMed
  • 41 Jacobi von Wangelin A, Neumann H, Gördes D, Spannenberg A, Beller M. Org. Lett. 2001; 3: 2895
    PubMed
  • 42 Klaus S, Hübner S, Neumann H, Strübing D, Jacobi von Wangelin A, Gördes D, Beller M. Adv. Synth. Catal. 2004; 346: 970
  • 43 Strübing D, Neumann H, Klaus S, Hübner S, Beller M. Tetrahedron 2005; 61: 11333
  • 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
    PubMed
  • 47 Menezes RF, Zezza CA, Sheu J, Smith MB. Tetrahedron Lett. 1989; 30: 3295
  • 48 Hübner S, Michalik D, Jiao H, Neumann H, Klaus S, Strübing D, Spannenberg A, Beller M. Chem.–Asian J. 2007; 2: 734
    PubMed
  • 49 Smith CD, Batey RA. Tetrahedron 2008; 64: 652
  • 50 Gerencsér J, Dormán G, Darvas F. QSAR Comb. Sci. 2006; 25: 439
  • 51 Simon C, Constantieux T, Rodriguez J. Eur. J. Org. Chem. 2004; 4957
  • 52 Tietze LF, Beifuss U. Angew. Chem. Int. Ed. Engl. 1993; 32: 131
  • 53 Tietze LF, Meier H, Nutt H. Liebigs Ann. Chem. 1990; 253
  • 54 Tietze LF, Meier H, Nutt H. Chem. Ber. 1989; 643
  • 55 Tietze LF, Bachmann J, Schul W. Angew. Chem. Int. Ed. Engl. 1988; 27: 971
  • 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
  • 60 Radi M, Bernardo V, Bechi B, Castagnolo D, Pagano M, Botta M. Tetrahedron Lett. 2009; 50: 6572
  • 61 Prajapati D, Gohain M. Beilstein J. Org. Chem. 2006; 2: 11
    PubMed
  • 62 Palasz A. Synthesis 2010; 4021
  • 63 Tietze LF, Evers H, Töpken E. Angew. Chem. Int. Ed. 2001; 40: 903
    PubMed
  • 64 Tietze LF, Evers H, Töpken E. Helv. Chim. Acta 2002; 85: 4200
  • 65 Nandaluru PR, Bodwell GJ. Org. Lett. 2012; 14: 310
    PubMed
  • 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
    PubMed
  • 68 Dediu OG, Yehia NAM, Oeser T, Polborn K, Müller TJJ. Eur. J. Org. Chem. 2005; 1834
  • 69 Presset M, Coquerel Y, Rodriguez J. Org. Lett. 2009; 11: 5706
    PubMed
  • 70 Harris GH, Graham AE. Tetrahedron Lett. 2010; 51: 6890
  • 71 Zou Y, Wang Q, Goeke A. Chem.–Eur. J. 2008; 14: 5335
    PubMed
  • 72 Ramachary DB, Chowdari NS, Barbas III CF. Synlett 2003; 1910
  • 73 Ramachary DB, Chowdari NS, Barbas III CF. Angew. Chem. Int. Ed. 2003; 42: 4233
    PubMed
  • 74 Pizzirani D, Roberti M, Recanatini M. Tetrahedron Lett. 2007; 48: 7120
  • 75 Ramachary DB, Barbas III CF. Chem.–Eur. J. 2004; 10: 5323
    PubMed
  • 76 Ramachary DB, Reddy YV, Banerjee A, Banerjee S. Org. Biomol. Chem. 2011; 9: 7282
    PubMed
  • 77 Shi J, Liu Y, Wang M, Lin L, Liu X, Feng X. Tetrahedron 2011; 67: 1781