Perspectives on Intermolecular Azomethine Ylide [3+2] Cycloadditions with Non-Electrophilic Olefins

^‡ The authors contributed equally.

Dedicated to Prof. Paul Knochel.

Abstract

Our interest in the synthesis of compact nitrogen heterocycles from abundant sources has motivated a critical analysis of the status in azomethine ylide chemistry. Despite the outstanding developments in catalytic enantioselective [3+2] cycloadditions, these are still limited to electron-poor olefins. Only a few examples can be found in the literature that report on cycloadditions using non-electrophilic alkenes and those are compiled herein. With this account we aim to extract lessons and challenges that will inspire future breakthroughs in this area.

1 Introduction

2 State-of-the-Art Using Electron-Poor Olefins

3 Research on Activated Non-Electrophilic Olefins

3.1 Aromatic Olefins

3.2 Polyenes

3.3 Hetero-Substituted Olefins

3.4 Rare Examples with Alkyl-Substituted Olefins: Norbornadiene and Tethered α-Olefins

4 Extracted Generalities

4.1 Kinetic Barrier to Non-Electrophilic Olefins

4.2 Charge Concentration: An Unsolved Thermodynamic Penalty

5 Conclusions and Outlook

Key words

heterocycles - pyrrolidines - anionic cycloaddition - azomethine ylide - catalysis

• References

• 1a Melchiorre P, Marigo M, Carlone A, Bartoli G. Angew. Chem. Int. Ed. 2008; 47: 6138
• 1b Mukherjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471
• 1c Doyle AG, Jacobsen EN. Chem. Rev. 2007; 107: 5713
• 1d Jurberg ID, Chatterjee I, Tannert R, Melchiorre P. Chem. Commun. 2013; 49: 4869
• 1e Albrecht Ł, Jiang H, Jørgensen KA. Chem. Eur. J. 2014; 20: 358
• 1f Meninno S, Lattanzi A. Chem. Commun. 2013; 49: 3821
• 1g Buchner E. Ber. Dtsch. Chem. Ges. 1888; 21: 2637
• 1h Palomo C, Mielgo A. Angew. Chem. Int. Ed. 2006; 45: 7876
• 1i Jensen KL, Dickmeiss G, Jiang H, Albrecht Ł, Jørgensen KA. Acc. Chem. Res. 2012; 45: 248
• 1j Erkkilä A, Majander I, Pihko PM. Chem. Rev. 2007; 107: 5416
• 2a Cho BT. Chem. Soc. Rev. 2009; 38: 443
• 2b Vargas-Caporali J, Juaristi E. Synthesis 2016; 48: 3890
• 2c Corey EJ, Bakshi RK, Shibata S. J. Am. Chem. Soc. 1987; 109: 5551
• 3 Chen MS, White MC. Science (Washington, D. C.) 2007; 318: 783
• 4a Nájera C, Sansano JM. Angew. Chem. Int. Ed. 2005; 44: 6272
• 4b Pandey G, Banerjee P, Gadre SR. Chem. Rev. 2006; 106: 4484
• 4c Adrio J, Carretero JC. Chem. Commun. 2011; 47: 6784
• 4d Adrio J, Carretero JC. Chem. Commun. 2014; 50: 12434
• 4e Narayan R, Potowski M, Jia Z.-J, Antonchick AP, Waldmann H. Acc. Chem. Res. 2014; 47: 1296
• 4f Wang LJ, Tang Y In Comprehensive Organic Synthesis II . Knochel P, Molander GA. Elsevier; Amsterdam: 2014
• 4g Hashimoto T, Maruoka K. Chem. Rev. 2015; 115: 5366
• 5a Suárez-Pantiga S, Colas K, Johansson MJ, Mendoza A. Angew. Chem. Int. Ed. 2015; 54: 14094
• 5b Mendoza A, Colas K, Suárez-Pantiga S, Götz DC. G, Johansson MJ. Synlett 2016; 27: 1753
• 6a Filippone S, Maroto EE, Martín-Domenech A, Suarez M, Martín N. Nat. Chem. 2009; 1: 578
• 6b Maroto EE, de Cózar A, Filippone S, Martín-Domenech Á, Suarez M, Cossío FP, Martín N. Angew. Chem. Int. Ed. 2011; 50: 6060
• 6c Sawai K, Takano Y, Izquierdo M, Filippone S, Martin N, Slanina Z, Mizorogi N, Waelchli M, Tsuchiya T, Akasaka T, Nagase S. J. Am. Chem. Soc. 2011; 133: 17746
• 7 Allway P, Grigg R. Tetrahedron Lett. 1991; 32: 5817
• 8 Longmire JM, Wang B, Zhang X. J. Am. Chem. Soc. 2002; 124: 13400
• 9 Gothelf AS, Gothelf KV, Hazell RG, Jørgensen KA. Angew. Chem. Int. Ed. 2002; 41: 4236
• 10 Chen C, Li X, Schreiber SL. J. Am. Chem. Soc. 2003; 125: 10174
• 11 Knöpfel TF, Aschwanden P, Ichikawa T, Watanabe T, Carreira EM. Angew. Chem. Int. Ed. 2004; 43: 5971
• 12a Cabrera S, Arrayás RG, Carretero JC. J. Am. Chem. Soc. 2005; 127: 16394
• 12b López-Pérez A, Adrio J, Carretero JC. Angew. Chem. Int. Ed. 2009; 48: 340
• 12c Hernández-Toribio J, Padilla S, Adrio J, Carretero JC. Angew. Chem. Int. Ed. 2012; 51: 8854
• 13 Zeng W, Zhou YG. Org. Lett. 2005; 7: 5055
• 14 Yan XX, Peng Q, Zhang Y, Zhang K, Hong W, Hou XL, Wu YD. Angew. Chem. Int. Ed. 2006; 45: 1979
• 15 Zeng W, Chen GY, Zhou YG, Li YX. J. Am. Chem. Soc. 2007; 129: 750
• 16a Melhado AD, Luparia M, Toste FD. J. Am. Chem. Soc. 2007; 129: 12638
• 16b Melhado AD, Amarante GW, Wang ZJ, Luparia M, Toste FD. J. Am. Chem. Soc. 2011; 133: 3517
• 17a Saito S, Tsubogo T, Kobayashi S. J. Am. Chem. Soc. 2007; 129: 5364
• 17b Yamashita Y, Guo XX, Takashita R, Kobayashi S. J. Am. Chem. Soc. 2010; 132: 3262
• 17c Yamashita Y, Imaizumi T, Kobayashi S. Angew. Chem. Int. Ed. 2011; 50: 4893
• 18a Nájera C, Retamosa MdG, Sansano JM. Angew. Chem. Int. Ed. 2008; 47: 6055
• 18b Martín-Rodríguez M, Nájera C, Sansano JM, Wu F.-L. Tetrahedron: Asymmetry 2010; 21: 1184
• 18c Castelló LM, Nájera C, Sansano JM, Larrañaga O, de Cózar A, Cossío FP. Org. Lett. 2013; 15: 2902
• 18d Nájera C, de Gracia Retamosa M, Sansano JM. Org. Lett. 2007; 9: 4025
• 19a Wang CJ, Liang G, Xue ZY, Gao F. J. Am. Chem. Soc. 2008; 130: 17250
• 19b Xue Z.-Y, Liu T.-L, Lu Z, Huang H, Tao H.-Y, Wang C.-J. Chem. Commun. 2010; 46: 1727
• 19c Li Q.-H, Liu T.-L, Wei L, Zhou X, Tao H.-Y, Wang C.-J. Chem. Commun. 2013; 49: 9642
• 20 Oura I, Shimizu K, Ogata K, Fukuzawa SI. Org. Lett. 2010; 12: 1752
• 21 Arai T, Yokoyama N, Mishiro A, Sato H. Angew. Chem. Int. Ed. 2010; 49: 7895
• 22 Zhang C, Yu SB, Hu XP, Wang DY, Zheng Z. Org. Lett. 2010; 12: 5542
• 23a Antonchick AP, Gerding-Reimers C, Catarinella M, Schürmann M, Preut H, Ziegler S, Rauh D, Waldmann H. Nat. Chem. 2010; 2: 735
• 23b Potowski M, Schürmann M, Preut H, Antonchick AP, Waldmann H. Nat. Chem. Biol. 2012; 8: 428
• 23c Narayan R, Bauer JO, Strohmann C, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2013; 52: 12892
• 23d Vidadala SR, Golz C, Strohmann C, Daniliuc CG, Waldmann H. Angew. Chem. Int. Ed. 2015; 54: 651
• 24 Vicario JL, Reboredo S, Badía D, Carrillo L. Angew. Chem. Int. Ed. 2007; 46: 5168
• 25a Chen XH, Zhang WQ, Gong LZ. J. Am. Chem. Soc. 2008; 130: 5652
• 25b Chen XH, Wei Q, Luo SW, Xiao H, Gong LZ. J. Am. Chem. Soc. 2009; 131: 13819
• 26a Liu YK, Liu H, Du W, Yue L, Chen YC. Chem. Eur. J. 2008; 14: 9873
• 26b Sun W, Zhu G, Wu C, Li G, Hong L, Wang R. Angew. Chem. Int. Ed. 2013; 52: 8633
• 27a Kauffmann T, Berg H, Köppelmann E. Angew. Chem., Int. Ed. Engl. 1970; 9: 380
• 27b Kauffmann T. Angew. Chem., Int. Ed. Engl. 1974; 13: 627
• 28 Pandiancherri S, Lupton DW. Tetrahedron Lett. 2011; 52: 671
• 29 Kauffmann T, Habersaat K, Koeppelmann E. Chem. Ber. 1977; 110: 638
• 30 Tsuge O, Kanemasa S, Hatada A, Matsuda K. Bull. Chem. Soc. Jpn. 1986; 59: 2537
• 31a Pearson WH, Stevens EP. J. Org. Chem. 1998; 63: 9812
• 31b Pearson WH, Szura DP, Postich MJ. J. Am. Chem. Soc. 1992; 114: 1329
• 32a Pearson WH, Lian BW. Angew. Chem. Int. Ed. 1998; 37: 1724
• 32b Pearson WH. Pure Appl. Chem. 2002; 74: 1339
• 32c Pearson WH, Stoy P. Synlett 2003; 903
• 33 Pearson WH, Stevens EP, Aponick A. Tetrahedron Lett. 2001; 42: 7361
• 34a Kauffmann T, Eidenschink R. Angew. Chem., Int. Ed. Engl. 1971; 10: 739
• 34b Kauffmann T, Eidenschink R. Chem. Ber. 1977; 110: 645
• 35 Pearson WH, Mans DM, Kampf JW. J. Org. Chem. 2004; 69: 1235
• 36a Bower DJ, Howden ME. H. J. Chem. Soc., Perkin Trans. 1 1980; 672
• 36b Pearson WH, Mans DM, Kampf JW. Org. Lett. 2002; 4: 3099
• 37 Popowski E. Z. Chem. 1974; 14: 360
• 38a Kauffmann T, Ahlers H, Hamsen A, Schulz H, Tilhard HJ, Vahrenhorst A. Angew. Chem., Int. Ed. Engl. 1977; 16: 119
• 38b Kauffmann T, Ahlers H, Echsler KJ, Schulz H, Tilhard HJ. Chem. Ber. 1985; 118: 4496
• 39 Pearson WH, Mi Y, Lee IY, Stoy P. J. Am. Chem. Soc. 2001; 123: 6724
• 40 Pearson WH, Walters MA, Oswell KD. J. Am. Chem. Soc. 1986; 108: 2769
• 41 Kamata K, Terashima M. Heterocycles 1980; 14: 205
• 42a Neumann F, Lambert C, Schleyer PvR. J. Am. Chem. Soc. 1998; 120: 3357
• 42b Freeman F, Dang P, Huang AC, Mack A, Wald K. Tetrahedron Lett. 2005; 46: 1993
• 42c Kuznetsov ML. Russ. Chem. Rev. 2006; 75: 935
• 43 Coldham I, Hufton R. Chem. Rev. 2005; 105: 2765
• 44a Kauffmann T, Eidenschink R. Angew. Chem., Int. Ed. Engl. 1973; 12: 568
• 44b Kauffmann T, Eidenschink R. Chem. Ber. 1977; 110: 651
• 44c Kauffmann T, Busch A, Habersaat K, Koeppelmann E. Chem. Ber. 1983; 116: 492