2.1.7 [4 + 2] Cycloaddition as the Key Step

M. Elliott; D. H. Jones

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

• 1 Posner GH. Chem. Rev. 1986; 86: 831

• 2 Isambert N, Lavilla R. Chem.–Eur. J. 2008; 14: 8444

• 3 Lin C, Fang H, Tu Z, Liu J.-T, Yao C.-F. J. Org. Chem. 2006; 71: 6588

• 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

• 7 Kouznetsov VV. Tetrahedron 2009; 65: 2721

• 8 Kudale AA, Kendall J, Miller DO, Collins JL, Bodwell GJ. J. Org. Chem. 2008; 73: 8437

• 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

• 11 Notz W, Takana F, Barbas III CF. Acc. Chem. Res. 2004; 37: 580

• 12 Enders D, Hüttl MRM, Runsink J, Raabe G, Wendt B. Angew. Chem. Int. Ed. 2007; 46: 467

• 13 Paulvannan K. Tetrahedron Lett. 1999; 40: 1851

• 14 Paulvannan K. J. Org. Chem. 2004; 69: 1207

• 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

• 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

• 22 Zhang L, Malinakova HC. J. Org. Chem. 2007; 72: 1484

• 23 Sunderhaus JD, Dockendorff C, Martin SF. Org. Lett. 2007; 9: 4223

• 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

• 26 Duan S, Sinha-Mahapatra DK, Herndon JW. Org. Lett. 2008; 10: 1541

• 27 Roy P, Ghorai BK. Beilstein J. Org. Chem. 2010; 6: 52

• 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

• 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

• 35 Lee H.-Y, Kim HY, Tae H, Kim BG, Lee J. Org. Lett. 2003; 5: 3439

• 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

• 39 Lee PH, Lee K, Kang Y. J. Am. Chem. Soc. 2006; 128: 1139

• 40 de Meijere A, Nüske H, Es-Sayed M, Labahn T, Schroen T, Bräse S. Angew. Chem. Int. Ed. 1999; 38: 3669

• 41 Jacobi von Wangelin A, Neumann H, Gördes D, Spannenberg A, Beller M. Org. Lett. 2001; 3: 2895

• 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

• 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

• 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

• 62 Palasz A. Synthesis 2010; 4021

• 63 Tietze LF, Evers H, Töpken E. Angew. Chem. Int. Ed. 2001; 40: 903

• 64 Tietze LF, Evers H, Töpken E. Helv. Chim. Acta 2002; 85: 4200

• 65 Nandaluru PR, Bodwell GJ. Org. Lett. 2012; 14: 310

• 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

• 69 Presset M, Coquerel Y, Rodriguez J. Org. Lett. 2009; 11: 5706

• 70 Harris GH, Graham AE. Tetrahedron Lett. 2010; 51: 6890

• 71 Zou Y, Wang Q, Goeke A. Chem.–Eur. J. 2008; 14: 5335

• 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

• 74 Pizzirani D, Roberti M, Recanatini M. Tetrahedron Lett. 2007; 48: 7120

• 75 Ramachary DB, Barbas III CF. Chem.–Eur. J. 2004; 10: 5323

• 76 Ramachary DB, Reddy YV, Banerjee A, Banerjee S. Org. Biomol. Chem. 2011; 9: 7282

• 77 Shi J, Liu Y, Wang M, Lin L, Liu X, Feng X. Tetrahedron 2011; 67: 1781