Download PDF
Müller, T. J. J.: 2014 Science of Synthesis, 2013/6: Multicomponent Reactions, Volume 2 DOI: 10.1055/sos-SD-211-00080
Multicomponent Reactions, Volume 2

2.2.2 [4 + 2] Cycloaddition

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

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

Also available at
 


Abstract

The Diels–Alder reaction, with its diverse and extremely rich synthetic potential, is a powerful protocol in synthetic strategies toward natural and unnatural carbo- and heterocycles. This chapter describes multicomponent reaction sequences in which a [4 + 2]-cycloaddition reaction is a key step. In contrast to Section 2.1.7, the focus here is on cycloaddition reactions not involving α, β-unsaturated carbonyl compounds. Examples are described both where the [4 + 2] cycloaddition is the first step in the multicomponent sequence and where the [4 + 2] cycloaddition is a later step in the sequence, with the requisite diene and/or dienophile being formed in the initial steps.

Key words

Diels–Alder reaction - cycloaddition - dienes - heterodienes - dienophiles - carbocycles - heterocycles - allylboration - hydrovinylation - Povarov reaction - Knoevenagel reaction
 
  • 1 Inanaga K, Takasu K, Ihara M. J. Am. Chem. Soc. 2004; 126: 1352
    PubMed
  • 2 Rodríguez Brasco MF, Seldes AM, Palermo JA. Org. Lett. 2001; 3: 1415
    PubMed
  • 3 Hilt G, Lüers S, Smolko KI. Org. Lett. 2005; 7: 251
    PubMed
  • 4 Erver F, Hilt G. Org. Lett. 2012; 14: 1884
    PubMed
  • 5 Megevand S, Moore J, Schenk K, Vogel P. Tetrahedron Lett. 2001; 42: 673
  • 6 Narkevitch V, Megevand S, Schenk K, Vogel P. J. Org. Chem. 2001; 66: 5080
    PubMed
  • 7 Narkevitch V, Schenk K, Vogel P. Angew. Chem. Int. Ed. 2000; 39: 1806
    PubMed
  • 8 Roulet J.-M, Puhr G, Vogel P. Tetrahedron Lett. 1997; 38: 6201
  • 9 Deguin B, Roulet J.-M, Vogel P. Tetrahedron Lett. 1997; 38: 6197
  • 10 Bouchez LC, Dubbaka SR, Turks M, Vogel P. J. Org. Chem. 2004; 69: 6413
    PubMed
  • 11 de Azevedo MBM, Greene AE. J. Org. Chem. 1995; 60: 4940
  • 12 Nebois P, Greene AE. J. Org. Chem. 1996; 61: 5210
  • 13 Kanazawa A, Delair P, Pourashraf M, Greene AE. J. Chem. Soc., Perkin Trans. 1 1997; 1911
  • 14 Tailor J, Hall DG. Org. Lett. 2000; 2: 3715
    PubMed
  • 15 Vaultier M, Truchet F, Carboni B, Hoffmann RW, Denne I. Tetrahedron Lett. 1987; 28: 4169
  • 16 Touré BB, Hoveyda HR, Tailor J, Ulaczyk-Lesanko A, Hall DG. Chem.–Eur. J. 2003; 9: 466
    PubMed
  • 17 Waldner A. Tetrahedron Lett. 1989; 30: 3061
  • 18 Touré BB, Hall DG. Angew. Chem. Int. Ed. 2004; 43: 2001
    PubMed
  • 19 Touré BB, Hall DG. J. Org. Chem. 2004; 69: 8429
    PubMed
  • 20 Gao X, Hall DG, Deligny M, Favre A, Carreaux F, Carboni B. Chem.–Eur. J. 2006; 12: 3132
    PubMed
  • 21 Gao X, Hall DG. J. Am. Chem. Soc. 2003; 125: 9308
    PubMed
  • 22 Deligny M, Carreaux F, Carboni B. Synlett 2005; 1462
  • 23 Gao X, Hall DG. J. Am. Chem. Soc. 2005; 127: 1628
    PubMed
  • 24 Denmark SE, Thorarensen A. Chem. Rev. 1996; 96: 137
    PubMed
  • 25 van Berkom LWA, Kuster GJT, Scheeren HW. Mol. Diversity 2003; 6: 271
    PubMed
  • 26 Avalos M, Babiano R, Cintas P, Higes FJ, Jiménez JL, Palacios JC, Silva MA. J. Org. Chem. 1999; 64: 1494
    PubMed
  • 27 Denmark SE, Hurd AR. J. Org. Chem. 2000; 65: 2875
    PubMed
  • 28 Denmark SE, Thorarensen A. J. Org. Chem. 1994; 59: 5672
  • 29 Denmark SE, Cottell JJ. J. Org. Chem. 2001; 66: 4276
    PubMed
  • 30 Denmark SE, Herbert B. J. Org. Chem. 2000; 65: 2887
    PubMed
  • 31 Zhu W, Mena M, Jnoff E, Sun N, Pasau P, Ghosez L. Angew. Chem. Int. Ed. 2009; 48: 5880
    PubMed
  • 32 Paulvannan K. Tetrahedron Lett. 1999; 40: 1851
  • 33 Sello JK, Andreana PR, Lee D, Schreiber SL. Org. Lett. 2003; 5: 4125
    PubMed
  • 34 Ilyin A, Kysil V, Krasavin M, Kurashvili I, Ivachtchenko AV. J. Org. Chem. 2006; 71: 9544
    PubMed
  • 35 Gámez-Montaño R, González-Zamora E, Potier P, Zhu J. Tetrahedron 2002; 58: 6351
  • 36 Bouma MJ, Masson G, Zhu J. Eur. J. Org. Chem. 2012; 475
  • 37 Neumann H, Jacobi von Wangelin A, Gördes D, Spannenberg A, Beller M. J. Am. Chem. Soc. 2001; 123: 8398
    PubMed
  • 38 Klaus S, Hübner S, Neumann H, Strübing D, Jacobi von Wangelin A, Gördes D, Beller M. Adv. Synth. Catal. 2004; 346: 970
  • 39 Strübing D, Neumann H, Jacobi von Wangelin A, Klaus S, Hübner S, Beller M. Tetrahedron 2006; 62: 10962
  • 40 Jacobi von Wangelin A, Neumann H, Gördes D, Klaus S, Jiao H, Spannenberg A, Krüger T, Wendler C, Thurow K, Stoll N, Beller M. Chem.–Eur. J. 2003; 9: 2273
    PubMed
  • 41 Neumann H, Jacobi von Wangelin A, Klaus S, Strübing D, Gördes D, Beller M. Angew. Chem. Int. Ed. 2003; 42: 4503
    PubMed
  • 42 Jacobi von Wangelin A, Neumann H, Gördes D, Spannenberg A, Beller M. Org. Lett. 2001; 3: 2895
    PubMed
  • 43 Strübing D, Kirschner A, Neumann H, Hübner S, Klaus S, Bornscheuer UT, Beller M. Chem.–Eur. J. 2005; 11: 4210
    PubMed
  • 44 Strübing D, Neumann H, Hübner S, Klaus S, Beller M. Org. Lett. 2005; 7: 4321
    PubMed
  • 45 Kouznetsov VV. Tetrahedron 2009; 65: 2721
  • 46 Povarov LS, Mikhailov BM. Izv. Akad. Nauk SSSR, Ser. Khim. 1963; 955 Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1963; 871
  • 47 Narasaka K, Shibata T. Heterocycles 1993; 35: 1039
  • 48 Kobayashi S, Ishitani H, Nagayama S. Synthesis 1995; 1195
  • 49 Batey RA, Simoncic PD, Lin D, Smyj RP, Lough AJ. Chem. Commun. (Cambridge) 1999; 651
  • 50 Annunziata R, Cinquini M, Cozzi F, Molteni V, Schupp O. Tetrahedron 1997; 53: 9715
  • 51 Das B, Reddy MR, Reddy VS, Ramu R. Chem. Lett. 2004; 33: 1526
  • 52 Li J, Li J, Su W. J. Chem. Res. 2009; 499
  • 53 Ma Y, Qian C, Xie M, Sun J. J. Org. Chem. 1999; 64: 6462
  • 54 Mahajan D, Ganai BA, Sharma RL, Kapoor KK. Tetrahedron Lett. 2006; 47: 7919
  • 55 Xia M, Lu Y.-d. Synlett 2005; 2357
  • 56 Maiti G, Kundu P. Tetrahedron Lett. 2006; 47: 5733
  • 57 Kumar RS, Nagarajan R, Perumal PT. Synthesis 2004; 949
  • 58 More SV, Sastry MNV, Yao C.-F. Synlett 2006; 1399
  • 59 Kamble VT, Davane BS, Chavan SA, Muley DB, Atkore ST. Chin. Chem. Lett. 2010; 21: 265
  • 60 Srinivas KVNS, Das B. Synlett 2004; 1715
  • 61 Liu RH, Yu X, Hu L, Yu NF. Chin. Chem. Lett. 2012; 23: 1027
  • 62 Batey RA, Powell DA, Acton A, Lough AJ. Tetrahedron Lett. 2001; 42: 7935
  • 63 Shao L.-X, Shi M. Adv. Synth. Catal. 2003; 345: 963
  • 64 Smith CD, Gavrilyuk JI, Lough AJ, Batey RA. J. Org. Chem. 2010; 75: 702
    PubMed
  • 65 He L, Bekkaye M, Retailleau P, Masson G. Org. Lett. 2012; 14: 3158
    PubMed
  • 66 Shi F, Xing G.-J, Tao Z.-L, Luo S.-W, Tu S.-J, Gong L.-Z. J. Org. Chem. 2012; 77: 6970
    PubMed
  • 67 Chen C.-H, Yellol GS, Lin P.-T, Sun C.-M. Org. Lett. 2011; 13: 5120
    PubMed
  • 68 Tietze LF, Hippe T, Steinmetz A. Synlett 1996; 1043
  • 69 Tietze LF. Chem. Rev. 1996; 96: 115
    PubMed
  • 70 Tietze LF, Rackelmann N, Müller I. Chem.–Eur. J. 2004; 10: 2722
    PubMed
  • 71 Bonne D, Coquerel Y, Constantieux T, Rodriguez J. Tetrahedron: Asymmetry 2010; 21: 1085
  • 72 Majumdar KC, Taher A, Nandi RK. Tetrahedron 2012; 68: 5693
  • 74 Prajapati D, Gohain M. Beilstein J. Org. Chem. 2006; 2: 11
    PubMed
  • 75 Jiménez-Alonso S, Estévez-Braun A, Ravelo ÁV, Zárate R, López M. Tetrahedron 2007; 63: 3066