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Synthesis 2013; 45(14): 1909-1930
DOI: 10.1055/s-0033-1338484
DOI: 10.1055/s-0033-1338484
review
Enantioselective Organocatalyzed Domino Synthesis of Six-Membered Carbocycles
Further Information
Publication History
Received: 18 February 2013
Accepted after revision: 08 April 2013
Publication Date:
06 June 2013 (online)
Dedicated to the elegant and stimulating realizations of Professor D. Enders in the field of this review
Abstract
Polysubstituted chiral cyclohexanes and cyclohexenes are important building blocks in organic synthesis. From historical and pioneering reports to the most recent accounts, this review focuses on domino enantioselective organocatalytic methodologies that have allowed the control of the relative and absolute configurations of up to six stereogenic centers in the construction of these versatile molecular architectures.
1 Introduction
2 Two-Component Transformations
2.1 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds
2.2 Michael-Initiated Domino Reactions with Nitroolefins
2.3 Non Michael-Initiated Domino Reactions
3 Multicomponent and Related Transformations
3.1 Pseudo-Three-Component Reactions
3.1.1 Michael-Initiated Domino Reactions with Nitroolefins
3.1.2 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds
3.2 Consecutive Reactions
3.2.1 Michael-Initiated Domino Reactions with Nitroolefins
3.2.2 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds
3.3 Multicomponent Reactions
3.3.1 Michael-Initiated Domino Reactions with Nitroolefins
3.3.2 Michael-Initiated Domino Reactions with α,β-Unsaturated Carbonyl Compounds
4 Conclusion
-
References
- 1 Kekulé A. Ann. Chem. Pharm. 1858; 106: 129
- 2 Couper AS. Ann. Chim. Phys. 1858; 53: 469
- 3 Six-Membered Carbocycles. In Name Reactions for Carbocyclic Ring Formations. Li JJ. John Wiley & Sons; Hoboken: 2010
-
5 Diels O, Alder K. Justus Liebigs Ann. Chem. 1928; 460: 98
- 6 Rapson WS, Robinson R. J. Chem. Soc. 1935; 1285
- 7 Schutlz AG. Acc. Chem. Res. 1990; 23: 207
- 8a For a review on organocatalytic Diels–Alder reactions, see: Merino P, Marqués-López E, Tejero T, Herrera RP. Synthesis 2010; 1
- 8b Tan B, Hernández-Torres G, Barbas III CF. J. Am. Chem. Soc. 2011; 133: 12354
- 8c Jia Z.-J, Jiang H, Li J.-L, Gschwend B, Li Q.-Z, Yin X, Grouleff J, Chen Y.-C, Jørgensen KA. J. Am. Chem. Soc. 2011; 133: 5053
- 9 Eder U, Sauer G, Wiechert R. Angew. Chem. Int. Ed. 1971; 10: 496
- 10 Hajos ZG, Parrish DR. J. Org. Chem. 1974; 39: 1615
- 11 Bui T, Barbas III CF. Tetrahedron Lett. 2000; 41: 6951
- 12a Ramachary DB, Chowdari NS, Barbas III CF. Angew. Chem. Int. Ed. 2003; 42: 4233
- 12b Ramachary DB, Anebouselvy K, Chowdari NS, Barbas III CF. J. Org. Chem. 2004; 69: 5838
- 12c For a related Knoevenagel–Diels–Alder sequence involving ynones instead of enones, see: Ramachary DB, Venkaiah C, Krishna PM. Chem. Commun. 2012; 48: 2252
- 13a Tietze LF, Rackelmann N, Müller I. Chem. Eur. J. 2004; 10: 2722
- 13b Sabitha G, Fatima N, Reddy EV, Yadav JS. Adv. Synth. Catal. 2005; 347: 1353
- 13c Khoshkholgh MJ, Balalaie S, Bijanzadeh HR, Rominiger F, Gross JH. Tetrahedron Lett. 2008; 49: 6965
- 14a Pellissier H. Adv. Synth. Catal. 2012; 354: 237
- 14b Moyano A, Rios R. Chem. Rev. 2011; 111: 4703
- 14c Grondal C, Jeanty M, Enders D. Nature Chem. 2010; 2: 167
- 14d Alba A.-N, Companyó X, Viciano M, Rios R. Curr. Org. Chem. 2009; 13: 1432
- 14e Enders D, Grondal C, Hüttl MR. M. Angew. Chem. Int. Ed. 2007; 46: 1570
- 15 Bonne D, Constantieux T, Coquerel Y, Rodriguez J. Chem. Eur. J. 2013; 19: 2218
- 16 Tsogoeva SB. Eur. J. Org. Chem. 2007; 1701
- 17a Yamaguchi M, Yokota N, Minami T.. J. Chem. Soc., Chem. Commun. 1991; 1088
- 17b Yamaguchi M, Shiraishi T, Hirama M. Angew. Chem., Int. Ed. Engl. 1993; 32: 1176
- 17c Yamaguchi M, Shiraishi T, Hirama M. J. Org. Chem. 1996; 61: 3520
- 18 Halland N, Aburel PS, Jørgensen KA. Angew. Chem. Int. Ed. 2003; 42: 661
- 19 Berner OM, Tedeschi L, Enders D. Eur. J. Org. Chem. 2002; 1877
- 20a List B, Pojarliev P, Martin HJ. Org. Lett. 2001; 3: 2423
- 20b List B. Acc. Chem. Res. 2004; 37: 548
- 21 Halland N, Aburel SP, Jørgensen KA. Angew. Chem. Int. Ed. 2004; 43: 1272
- 22 Pulkkinen J, Aburel PS, Halland N, Jørgensen KA. Adv. Synth. Catal. 2004; 346: 1077
- 23 Hayashi T, Toyoshima M, Gotoh H, Ishikawa H. Org. Lett. 2009; 11: 45
- 24 Carlone A, Marigo M, North C, Landa A, Jørgensen KA. Chem. Commun. 2006; 4928
- 25 Yang Y.-Q, Chai Z, Wang H.-F, Chen X.-K, Cui H.-F, Zheng C.-W, Xiao H, Li P, Zhao G. Chem. Eur. J. 2009; 15: 13295
- 26 Marigo M, Bertelsen B, Landa A, Jørgensen KA. J. Am. Chem. Soc. 2006; 128: 5475
- 27 Cao C.-L, Sun X.-L, Kang Y.-B, Tang Y. Org. Lett. 2007; 9: 4151
- 28 Wang X.-J, Zhao Y, Liu J.-T. Synthesis 2008; 3967
- 29 Yang H, Carter RG. Org. Lett. 2010; 12: 3108
- 30 Inokoishi Y, Sasakura N, Nakano K, Ichikawa Y, Kotsuki H. Org. Lett. 2010; 12: 1616
- 31 Zhao G.-L, Dziedzic P, Ullah F, Eriksson L, Córdova A. Tetrahedron Lett. 2009; 50: 3458
- 32 Hayashi Y, Okano T, Aratake S, Hazelard D. Angew. Chem. Int. Ed. 2007; 46: 4922
- 33 Enders D, Narine AA, Benninghaus TR, Raabe G. Synlett 2007; 1667
- 34 Enders D, Wang C, Bats JW. Synlett 2009; 1777
- 35 Anwar S, Chang H.-J, Chen K. Org. Lett. 2011; 13: 2200
- 36 Reyes E, Jiang H, Milelli A, Elsner P, Hazell RG, Jørgensen KA. Angew. Chem. Int. Ed. 2007; 46: 9202
- 37 Murphy JJ, Quintard A, McArdle P, Alexakis A, Stephens JC. Angew. Chem. Int. Ed. 2011; 50: 5095
- 38a Brandau S, Landa A, Franzén J, Marigo M, Jørgensen KA. Angew. Chem. Int. Ed. 2006; 45: 4305
- 38b Jensen KL, Dickmeiss G, Jiang H, Albrecht Ł, Jørgensen KA. Acc. Chem. Res. 2012; 45: 248
- 38c Mauro M, Wabnitz TC, Fielenbach D, Jørgensen KA. Angew. Chem. Int. Ed. 2005; 44: 794
- 38d Hayashi Y, Gotoh H, Hayashi T, Shoji M. Angew. Chem. Int. Ed. 2005; 44: 4212
- 39 Cabrera S, Aleman J, Bolze P, Bertelsen S, Jørgensen KA. Angew. Chem. Int. Ed. 2008; 47: 121
- 40 McGarraugh PG, Brenner SE. Org. Lett. 2009; 11: 5654
- 41 McGarraugh PG, Jones JH, Brenner-Moyer SE. J. Org. Chem. 2011; 76: 6309
- 42 Hong B.-C, Sadani AA, Roshan RY, Dange NS, Leeb G.-H. Synthesis 2011; 1887
- 43 Hong B.-C, Nimje RY, Lin C.-W, Liao J.-H. Org. Lett. 2011; 13: 1278
- 44 Hong B.-C, Liao W.-K, Dange NS, Liao J.-H. Org. Lett. 2013; 15: 468
- 45 Rajkumar S, Shankland K, Goodman JM, Cobb AJ. A. Org. Lett. 2013; 15: 1386
- 46 Xie J.-W, Chen W, Li R, Zeng M, Du W, Yue L, Chen Y.-C, Wu Y, Zhu J, Deng J.-G. Angew. Chem. Int. Ed. 2007; 46: 389
- 47 For a review on this family of catalysts, see: Melchiorre P, Marigo M, Carlone A, Bartoli G. Angew. Chem. Int. Ed. 2008; 47: 6138
- 48 Wu L.-Y, Bencivenni G, Mancinelli M, Mazzanti A, Bartoli G, Melchiorre P. Angew. Chem. Int. Ed. 2009; 48: 7196
- 49 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
- 50 Cassani C, Tian X, Escudero-Adán EC, Melchiorre P. Chem. Commun. 2011; 47: 233
- 51 Zhang J.-X, Li N.-K, Liu Z.-M, Huang X.-F, Geng Z.-C, Wang X.-W. Adv. Synth. Catal. 2013; 355: 797
- 52 Wei Q, Gong L.-Z. Org. Lett. 2010; 12: 1008
- 53a Li X.-M, Wang B, Zhang J.-M, Yan M. Org. Lett. 2011; 13: 374
- 53b De Fusco C, Lattanzi A. Eur. J. Org. Chem. 2011; 3728
- 54 Wu B, Liu G.-G, Li M.-Q, Zhang Y, Zhang S.-Y, Qiu J.-R, Xu X.-P, Ji S.-J, Wang X.-W. Chem. Commun. 2011; 47: 3992
- 55 Wang L.-L, Peng L, Bai J.-F, Jia L.-N, Luo X.-Y, Huang Q.-C, Xu X.-Y, Wang L.-X. Chem. Commun. 2011; 47: 5593
- 56a Wu B, Chen J, Li M.-Q, Zhang J.-X, Xu X.-P, Ji S.-J, Wang X.-W. Eur. J. Org. Chem. 2012; 1318
- 56b Li X, Yang C, Jin J.-L, Xue X.-S, Cheng J.-P. Chem. Asian J. 2013; 8: 997
-
57a Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606
- 57b Moore JL, Rovis T. Top. Curr. Chem. 2010; 291: 77
- 57c Bugaut X, Glorius F. Chem. Soc. Rev. 2012; 41: 3511
-
58 Nair V, Menon RS, Biju AT, Sinu CR, Paul RR, Jose A, Sreekumar V. Chem. Soc. Rev. 2011; 40: 5336
- 59 Fang X, Jiang K, Xing C, Hao L, Chi YR. Angew. Chem. Int. Ed. 2011; 50: 1910
- 60a Hoashi Y, Yabuta T, Takemoto Y. Tetrahedron Lett. 2004; 45: 9185
- 60b Hoashi Y, Yabuta T, Yuan P, Miyabe H, Takemoto Y. Tetrahedron 2006; 62: 365
- 61 Thayumanavan R, Dhevalapally B, Sakthivel K, Tanaka F, Barbas III CF. Tetrahedron Lett. 2002; 43: 3817
- 62 Yu D.-F, Wang Y, Xu P.-F. Adv. Synth. Catal. 2011; 353: 2960
- 63 Rajkumar S, Shankland K, Brown GD, Cobb AJ. A. Chem. Sci. 2012; 3: 584
- 64 Wang X.-F, Chen J.-R, Cao Y.-J, Cheng H.-G, Xiao W.-J. Org. Lett. 2010; 12: 1140
- 65 Cao C.-L, Zhou Y.-Y, Zhou J, Sun X.-L, Tang Y, Li Y.-X, Li G.-Y, Sun J. Chem. Eur. J. 2009; 15: 11384
- 66 Hong B.-C, Lan D.-J, Dange NS, Lee G.-H, Liao J.-H. Eur. J. Org. Chem. 2013; 2472
- 67 Wong CT. Tetrahedron 2012; 68: 481
- 68 Chintala P, Ghost SK, Long E, Headley AD, Ni B. Adv. Synth. Catal. 2011; 353: 2905
- 69 Hong B.-C, Kotame P, Liao J.-H. Org. Biomol. Chem. 2011; 9: 382
- 70 Tan B, Chua PJ, Li Y, Zhong G. Org. Lett. 2008; 10: 2437
- 71 Varga S, Jakab G, Drahos L, Holczbauer T, Czugler M, Soós T. Org. Lett. 2011; 13: 5416
- 72 Cagide-Fajín F, Nieto-García O, Lago-Santomé H, Alonso R. J. Org. Chem. 2012; 77: 11377
- 73 Zhou J, List B. J. Am. Chem. Soc. 2007; 129: 7498
- 74 Dai Q, Arman H, Zhao JC.-G. Chem. Eur. J. 2013; 19: 1666
- 75 Quintavalla A, Lombardo M, Sanap SP, Trombinia C. Adv. Synth. Catal. 2013; 355: 938
- 76a Beeson TD, Mastracchio A, Hong J, Ashton K, MacMillan DW. C. Science 2007; 316: 582
- 76b Jang H, Hong J, MacMillan DW. C. J. Am. Chem. Soc. 2007; 129: 7004
- 77 Jui NT, Lee EC. Y, MacMillan DW. C. J. Am. Chem. Soc. 2010; 132: 10015
- 78a Multicomponent Reactions. Zhu J, Bienaymé H. Wiley-VCH; Weinheim: 2005
- 78b Isambert N, Sanchez Duque MM, Plaquevent J.-C, Génisson Y, Rodriguez J, Constantieux T. Chem. Soc. Rev. 2011; 40: 1347
- 78c Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083
- 78d Shiri M. Chem. Rev. 2012; 112: 3508
- 78e Marson CM. Chem. Soc. Rev. 2012; 41: 7712
- 78f van Berkel SS, Bögels BG. M, Wijdeven MA, Westermann B, Rutjes FP. J. T. Eur. J. Org. Chem. 2012; 3543
- 78g de Graaff C, Ruijter E, Orru RV. A. Chem. Soc. Rev. 2012; 41: 3969
- 79a Yu X, Wang W. Org. Biomol. Chem. 2008; 6: 2037
- 79b Grossmann A, Enders D. Angew. Chem. Int. Ed. 2012; 51: 314
- 80 Enders D, Hüttl MR. M, Grondal C, Raabe G. Nature 2006; 441: 861
- 81 Jai Y, Mao Z, Wang R. Tetrahedron: Asymmetry 2011; 22: 2018
- 82 For a discussion on the terminology, see: Coquerel Y, Boddaert T, Presset M, Mailhol D, Rodriguez J. In Ideas in Chemistry and Molecular Sciences: Advances in Synthetic Chemistry. Pignataro B. Wiley-VCH; Weinheim: 2010. Chap. 9, 187
- 83a Baslé O, Raimondi W, Sanchez Duque MM, Bonne D, Constantieux T, Rodriguez J. Org. Lett. 2010; 12: 5246
- 83b Raimondi W, Sanchez Duque MM, Goudedranche S, Quintard A, Constantieux T, Bugaut X, Bonne D, Rodriguez J. Synthesis 2013; in press: DOI: 10.1055/s-0033-1338844
- 84 Mao Z, Jia Y, Xu Z, Wang R. Adv. Synth. Catal. 2012; 354: 1401
- 85 Rueping M, Haack KL, Ieawsuwan W, Sundén H, Blanco M, Schoepke FR. Chem. Commun. 2011; 47: 3828
- 86 Zeng X, Ni Q, Raabe G, Enders D. Angew. Chem. Int. Ed. 2013; 52: 2997
- 87 Carlone A, Cabrera S, Marigo M, Jørgensen KA. Angew. Chem. Int. Ed. 2007; 46: 1101
- 88 Enders D, Jeanty M, Bats JW. Synlett 2009; 3175
- 89 Companyó X, Zea A, Alba A-NR, Mazzanti A, Moyano A, Rios R. Chem. Commun. 2010; 46: 6953
- 90 Alba A.-NR, Zea A, Valero G, Calbet T, Font-Bardía M, Mazzanti A, Moyano A, Rios R. Eur. J. Org. Chem. 2011; 1318
- 91 Enders D, Greb A, Deckers K, Selig P, Merkens C. Chem. Eur. J. 2012; 18: 10226
- 92 Bertelsen S, Johansen RL, Jørgensen KA. Chem. Commun. 2008; 3016
- 93 Enders D, Urbanietz G, Cassens-Sasse E, Keeb S, Raabe G. Adv. Synth. Catal. 2012; 354: 1481
- 94 García Ruano JL, Marcos V, Suanzes JA, Marzo L, Alemán J. Chem. Eur. J. 2009; 15: 6576
- 95 Hong B.-C, Dange NS, Ding C.-F, Liao J.-H. Org. Lett. 2012; 14: 448
- 96a Enders D, Hüttl MR. M, Runsik Y, Raabe G, Wendt B. Angew. Chem. Int. Ed. 2007; 46: 467
- 96b Enders D, Hüttl MR. M, Raabe G, Bats JW. Adv. Synth. Catal. 2008; 350: 267
- 97 Enders D, Schmid B, Erdmann N. Synthesis 2010; 2271
- 98 Erdmann N, Philipps AR, Atodiresei I, Enders D. Adv. Synth. Catal. 2013; 355: 847
- 99 Wang Y, Han R.-G, Zhao Y.-L, Yang S, Xu P.-F, Dixon DJ. Angew. Chem. Int. Ed. 2009; 48: 9834
- 100 Zhou B, Yang Y, Shi J, Luo Z, Li Y. J. Org. Chem. 2013; 78: 2897
- 101 Tokoroyama T. Eur. J. Org. Chem. 2010; 2009
- 102a Jiang K, Jia Z.-J, Yin X, Chen S, Wu L, Chen Y.-C. Chem. Eur. J. 2010; 16: 2852
- 102b Jiang K, Jia Z.-J, Yin X, Wu L, Chen Y.-C. Org. Lett. 2010; 12: 2766
- 103 Zea A, Alba A.-NR, Mazzanti A, Moyano A, Rios R. Org. Biomol. Chem. 2011; 9: 6519
- 104a Bhanja Jena S, Nayak S, Mohapatra S. Beilstein J. Org. Chem. 2012; 8: 1668
- 104b Nising CF, Bräse S. Chem. Soc. Rev. 2012; 41: 988
- 105a Kotame P, Hong B.-C, Liao J.-H. Tetrahedron Lett. 2009; 50: 704
- 105b Hong B.-C, Kotame P, Tsai C.-W, Liao J.-H. Org. Lett. 2010; 12: 776
- 106 Zhang F.-L, Xu A.-W, Gong Y.-F, Wei M.-H, Yang X.-L. Chem. Eur. J. 2009; 15: 6815
For two elegant recent examples, see:
For the development of this strategy in the racemic series and synthetic applications, see:
For general reviews on organocascade reactions, see:
For an account, see:
For seminal reports on the use of diphenylprolinol silyl ethers as organocatalysts, see:
For selected reviews, see:
For some recent reviews, see:
For leading references, see refs. 14c, 14e and: