(4+1)-Cycloadditions Exploiting the Biphilicity of Oxyphosphonium Enolates and Rh^II/Pd^II-Stabilized Metallocarbenes for the Construction of Five-Membered Frameworks

Abstract

(4+1)-Cyclizations are an underutilized disconnect for the formation of five-membered heterocyclic and carbocyclic frameworks. Herein we analyze methods employing oxyphosphonium enolates and Rh^II/Pd^II-metallocarbenes as C1 synthons in the presence of several four-atom components for the synthesis of 2,3-dihydrobenzofurans, 2,3-dihydroindoles, oxazolones, cyclopentenones, and pyrrolones.

1 Introduction

2 (4+1)-Cyclizations Employing Kukhtin–Ramirez-Like Reactivity

3 (4+1)-Cyclizations Employing a Cyclopropanation/Ring-Expansion Sequence

4 Pd-Catalyzed (4+1)-Cyclizations through Carbene Migratory Insertion/Reductive Elimination Processes

5 Summary

Key words

(4+1)-cyclization - carbenes - rhodium - palladium - phosphorus - organocatalysis - carbocycles - heterocycles

Publication History

Received: 01 October 2020

Accepted after revision: 28 October 2020

Article published online:
26 January 2021

• References

• 1 Trost BM, Huang Z, Murhade GM. Science 2018; 362: 564
• 2 Organic Mechanisms: Reactions, Stereochemistry and Synthesis . Bruckner R, Harmata M. Springer; Berlin: 2010: 643
• 3 Herndon WC. Chem. Rev. 1972; 72: 157
• 4 Lautens M, Klute W, Tam W. Chem. Rev. 1996; 96: 49
• 5 Gothelf KV, Jørgensen KA. Chem. Rev. 1998; 98: 863
• 6 Frühauf H.-W. Chem. Rev. 1997; 97: 523
• 7 Hashimoto T, Maruoka K. Chem. Rev. 2015; 115: 536
• 8 Moyano A, Rios R. Chem. Rev. 2011; 111: 4703
• 9 Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
• 10 Lednicer D. Strategies for Organic Drug Synthesis and Design . John Wiley & Sons; Hoboken: 2008: 239
• 11 Baldwin JE. J. Chem. Soc., Chem. Commun. 1976; 734
• 12 Johnson CD. Acc. Chem. Res. 1993; 26: 476
• 13 Blanco-Urgoiti J, Añorbe L, Pérez-Serrano L, Domínguez G, Pérez-Castells J. Chem. Soc. Rev. 2004; 33: 32
• 14 Chen J.-R, Hu X.-Q, Lu L.-Q, Xiao W.-J. Chem. Rev. 2015; 115: 5301
• 15 Rodriguez KX, Vail JD, Ashfeld BL. Org. Lett. 2016; 18: 4514
• 16 Eckert KE, Lepore AJ, Ashfeld BL. Helv. Chim. Acta 2019; 102: e1900192
• 17 Eckert KE, Ashfeld BL. Org. Lett. 2018; 20: 2315
• 18 Rodriguez KX, Pilato TC, Ashfeld BL. Chem. Sci. 2018; 9: 3221
• 19 Meloche JL, Ashfeld BL. Angew. Chem. Int. Ed. 2017; 56: 6604
• 20a Ramirez F, Desai NB, Ramanathan N. Tetrahedron Lett. 1963; 4: 323
• 20b Ramirez F, Smith CP. J. Am. Chem. Soc. 1967; 89: 3030
• 20c Ramirez F, Telefus CD, Prasad VA. V. Tetrahedron 1975; 31: 2007
• 20d Ramirez F, Telefus CD. J. Org. Chem. 1969; 34: 376
• 21a Zhao W, Fink DM, Labutta CA, Radosevich AT. Org. Lett. 2013; 15: 3090
• 21b Wang SR, Radosevich AT. Org. Lett. 2015; 17: 3810
• 21c Miller EJ, Zhao W, Herr JD, Radosevich AT. Angew. Chem. Int. Ed. 2012; 51: 10605
• 21d Guo HC, Xu QH, Kwon O. J. Am. Chem. Soc. 2009; 131: 6318
• 21e Nykaza TV, Harrison TS, Ghosh A, Putnik RA, Radosevich AT. J. Am. Chem. Soc. 2017; 139: 639
• 21f Zhao W, Yan PK, Radosevich AT. J. Am. Chem. Soc. 2015; 137: 616
• 21g Zhao W, Radosevich AT. Org. Synth. 2015; 92: 267
• 21h Wang SR, Radosevich AT. Org. Lett. 2013; 15: 1926
• 22 Fleury LM, Wilson EE, Vogt M, Fan TJ, Oliver AG, Ashfeld BL. Angew. Chem. Int. Ed. 2013; 52: 11589
• 23 Willis NJ, Bray CD. Chem. Eur. J. 2012; 18: 9160
• 24 Izquierdo J, Orue A, Scheidt KA. J. Am. Chem. Soc. 2013; 135: 10634
• 25 Green JC, Jiménez-Alonso S, Brown ER, Pettus TR. R. Org. Lett. 2011; 13: 5500
• 26 Walden DM, Jaworski AA, Johnston RC, Hovey MT, Baker HV, Meyer MP, Scheidt KA, Cheong PH.-Y. J. Org. Chem. 2017; 82: 7183
• 27 Lee A, Younai A, Price CK, Izquierdo J, Mishra RK, Scheidt KA. J. Am. Chem. Soc. 2014; 136: 10589
• 28 Guo Z, Jia H, Liu H, Wang Q, Huang J, Guo H. Org. Lett. 2018; 20: 2939
• 29a Sutin L, Andersson S, Bergquist L, Castro VM, Danielsson E, James S, Henriksson M, Johansson L, Kaiser C, Flyren K, Williams M. Bioorg. Med. Chem. Lett. 2007; 17: 4837
• 29b Lee CM, Plotnikoff NP. J. Med. Chem. 1976; 19: 731
• 29c Dolente C, Fasching B, Runtz-Schmitt V, Schnider P. CA2929488A1, 2015
• 29d Banerjee RG, Gupta RC, Tuli D, Rode M, Suthar B, Umrani D, Pathak P, Choksi T, Chaudhary A. WO2007032028A1, 2007
• 29e Shue YK. Tetrahedon Lett. 1996; 37: 6447
• 29f Schiff PL. Am. J. Pharm. Educ. 2006; 70: 98
• 30 Trost BM, Hirano K. Angew. Chem. Int. Ed. 2012; 51: 6480
• 31 Miller EJ, Zhao W, Herr JD, Radosevich AT. Angew. Chem. Int. Ed. 2012; 51: 10605
• 32 Ford A, Miel H, Ring A, Slattery CN, Maguire AR, McKervey MA. Chem. Rev. 2015; 115: 9981
• 33 Lebel H, Marcoux JF, Molinaro C, Charette AB. Chem. Rev. 2003; 103: 977
• 34 Xiang Y, Wang C, Ding Q, Peng Y. Adv. Synth. Catal. 2019; 361: 919
• 35 Ebner C, Carreira EM. Chem. Rev. 2017; 117: 11651
• 36 Wu W, Lin Z, Jiang H. Org. Biomol. Chem. 2018; 16: 7315
• 37 Baldwin JE. Chem. Rev. 2003; 103: 1197
• 38a Trost BM, Bogdanowicz MJ. J. Am. Chem. Soc. 1973; 95: 5311
• 38b Danheiser RL, Martinez-Davila C, Morin JM. J. Org. Chem. 1980; 45: 1340
• 38c Danheiser RL, Bronson JJ, Okano K. J. Am. Chem. Soc. 1985; 107: 4579
• 38d Larsen SD. J. Am. Chem. Soc. 1988; 110: 5932
• 39a Davie CP, Danheiser RL. Angew. Chem. Int. Ed. 2005; 44: 5867
• 39b Austin WF, Zhang Y, Danheiser RL. Org. Lett. 2005; 7: 3905
• 39c Dalton AM, Zhang Y, Davie CP, Danheiser RL. Org. Lett. 2002; 4: 2465
• 39d Loebach JL, Bennett DM, Danheiser RL. J. Org. Chem. 1998; 63: 8380
• 39e Loebach JL, Bennett DM, Danheiser RL. J. Am. Chem. Soc. 1998; 120: 9690
• 39f Danheiser RL, Sard H. J. Org. Chem. 1980; 45: 4810
• 39g Tidwell TT. Ketenes . Wiley & Sons; New York: 1995: 682
• 39h Berkowitz WF, Ozorio AA. J. Org. Chem. 1975; 40: 527
• 40a Rigby JH, Wang Z. Org. Lett. 2003; 5: 263
• 40b Rigby JH, Wang Z. Org. Lett. 2002; 4: 4289
• 40c Rigby JH, Dong W. Org. Lett. 2000; 2: 1673
• 40d Rigby JH, Laurent S. J. Org. Chem. 1999; 64: 1766
• 40e Rigby JH, Qabar M. J. Am. Chem. Soc. 1991; 113: 8975
• 40f Rigby JH, Qabar M, Ahmed G, Hughes RC. Tetrahedron 1993; 49: 10219
• 40g Rigby JH. Synlett 2000; 1
• 41 Rodriguez KX, Kaltwasser N, Toni TA, Ashfeld BL. Org. Lett. 2017; 19: 2482
• 42 Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165
• 43 Panda SS, Jones RA, Bachawala P, Mohapatra PP. Mini Rev. Med. Chem. 2017; 17: 1515
• 44 Hansen J, Davies HM. L. Coord. Chem. Rev. 2008; 252: 545
• 45 Kniežo L, Kristian P, Imrich J, Ugozzoli F, Andreetti GD. Tetrahedron 1988; 44: 543
• 46 Rigby JH, Holsworth DD, James K. J. Org. Chem. 1989; 54: 4019
• 47a Greenman KL, Carter DS, Van Vranken DL. Tetrahedron 2001; 57: 5219
• 47b Barluenga J, Moriel P, Valdés C, Aznar F. Angew. Chem. Int. Ed. 2007; 46: 5587
• 47c Chen S, Wang J. Chem. Commun. 2008; 4198
• 47d Xiao Q, Ma J, Yang Y, Zhang Y, Wang J. Org. Lett. 2009; 11: 4732
• 47e Xia Y, Hu F, Xia Y, Liu Z, Ye F, Zhang Y, Wang J. Synthesis 2017; 49: 1073
• 48a Zhao X, Jing J, Lu K. Zhang Y., Wang J. 2010; 46: 1724
• 48b Tsoi Y.-T, Zhou Z, Chan AS. C, Yu W.-Y. Org. Lett. 2010; 12: 4506
• 48c Kitamura M, Sakata R, Okauchi T. Tetrahedron Lett. 2011; 52: 1931
• 49a Devine SK. J, Van Vranken DL. Org. Lett. 2007; 9: 2047
• 49b Devine SK. J, Van Vranken DL. Org. Lett. 2008; 10: 1909
• 49c Xia Y, Xia Y, Zhang Y, Wang J. Org. Biomol. Chem. 2014; 12: 9333
• 49d Shang XS, Li NT, Siyang HX, Liu PN. J. Org. Chem. 2015; 80: 4808
• 50a Trost BM. Acc. Chem. Res. 1990; 23: 34
• 50b Trost BM. Chem. Eur. J. 1998; 4: 2405
• 51 Tucker ZD, Hill HM, Smith AL, Ashfeld BL. Org. Lett. 2020; 22: 6605
• 52 Xia Y, Wang J. Chem. Soc. Rev. 2017; 46: 2306
• 53a Wang C, Pahadi N, Tunge JA. Tetrahedron 2009; 65: 5102
• 53b Li T.-R, Tan F, Lu L.-Q, Wei Y, Wang Y.-N, Liu Y.-Y, Yang Q.-Q, Chen J.-R, Shi D.-Q, Xiao W.-J. Nat. Commun. 2014; 5: 5500
• 54a Qu Z, Shi W, Wang J. J. Org. Chem. 2001; 66: 8139
• 54b Maxwell JL, Brown KC, Bartley DW, Kodadek T. Science 1992; 256: 1544