Recent Advances in the Application of Ring-Closing Metathesis for the Synthesis of Unsaturated Nitrogen Heterocycles

Emilia J. Groso; Corinna S. Schindler

doi:10.1055/s-0037-1611651

Synthesis, Inhaltsverzeichnis

CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1100-1114
DOI: 10.1055/s-0037-1611651

short review

Copyright with the author

Recent Advances in the Application of Ring-Closing Metathesis for the Synthesis of Unsaturated Nitrogen Heterocycles

Emilia J. Groso

,

Corinna S. Schindler *

Department of Chemistry, Willard Henry Dow Laboratory, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, USA eMail: corinnas@umich.edu

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

This short review summarizes recent advances relating to the application of ring-closing olefin-olefin and carbonyl-olefin metathesis reactions towards the synthesis of unsaturated five- and six-membered nitrogen heterocycles. These developments include catalyst modifications and reaction designs that will enable access to more complex nitrogen heterocycles.

1 Introduction

2 Expansion of Ring-Closing Metathesis Methods

3 Evaluation of Catalyst Design

4 Indenylidene Catalysts

5 Unsymmetrical N-Heterocyclic Carbene Ligands

6 Carbonyl-Olefin Metathesis

7 Conclusions

Key words

RCM - carbonyl-olefin metathesis - nitrogen heterocycles - catalyst design - ruthenium - Lewis acid catalysis

Volltext

Referenzen

References

For leading references, see:

1a Naturally Occurring Pyrrolizidine Alkaloids . Rizk A.-FM. CRC Press; Boca Raton: 1991
1b Mattocks AR. Chemistry and Toxicology of Pyrrolizidine Alkaloids. Academic Press; London: 1986
1c Bronner SM, Im G.-YJ, Garg NK. In Heterocycles in Natural Product Synthesis . Majumdar KC, Chattopadhyay SK. Wiley-VCH; Weinheim: 2011: 221
1d Michael JP. Nat. Prod. Rep. 2008; 25: 139
1e Michael JP. Alkaloids 2001; 55: 91
1f Li X, Li J. Mini-Rev. Med. Chem. 2010; 10: 794
1g Vikatu E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
1h Weintraub PM, Sabol JS, Kane JM, Borcherding DR. Tetrahedron 2003; 59: 2953
1i Mitchinson A, Nadin A. J. Chem. Soc., Perkin Trans. 1 2000; 2862 ; and earlier reviews in this series

2 Iminosugars: From Synthesis to Therapeutic Applications . Compain P, Martin OR. Wiley; Chichester: 2007

For the therapeutics listed in this review, see:

3a Hollmann M, Heinemann S. Annu. Rev. Neurosci. 1994; 17: 31
3b Iwanami S, Takashima M, Hirata Y, Haseqawa O, Usuda S. J. Med. Chem. 1981; 24: 1224
3c Maring C, McDaniel K, Krueger A, Zhao C, Sun M, Madigan D, DeGoey D, Chen J.-J, Yeung MC, Flosi W, Grampovnik D, Kati W, Klein L, Stewart K, Stoll V, Saldivar S, Montgomery D, Carrick R, Steffy K, Kempf D, Molla A, Kohlbrenner W, Kennedy A, Herrin T, Xu Y, Laver WG. Antiviral Res. 2001; 50: A76 ; Abstract 129
3d For more examples, see reference 1g.

4a Wurz RP, Fu GC. J. Am. Chem. Soc. 2005; 127: 12234
4b O’Hagan D. Nat. Prod. Rep. 2000; 17: 435

For examples, see:

5a Choi YH, Choi JY, Yange HY, Kim YH. Tetrahedron: Asymmetry 2002; 13: 801
5b Sweet JA, Cavallari JM, Price WA, Ziller JW, McGrath DV. Tetrahedron: Asymmetry 1997; 8: 207
5c Fache F, Schulz E, Tommasino ML, Lemaire M. Chem. Rev. 2000; 100: 2159

For examples, see:

6a Mukaiyamma T, Sakito Y, Asami M. Chem. Lett. 1979; 705
6b Enders D, Thiebes C. Pure Appl. Chem. 2001; 73: 573
6c Reisman SE, Doyle AG, Jacobsen EN. J. Am. Chem. Soc. 2008; 130: 7198
6d Dalko PI, Moisan L. Angew. Chem. Int. Ed. 2004; 43: 5138

7a Xu Z, Lu X. J. Org. Chem. 1998; 63: 5031
7b Hodgson DM, Miles TJ, Witherington J. Tetrahedron 2003; 59: 9729
7c Hong J, Zhang Z, Lei H, Cheng H, Hu Y, Yang W, Liang Y, Das D, Chen S.-H, Li G. Tetrahedron Lett. 2009; 50: 2525

8a Advances in Heterocyclic Chemistry, Vol. 115. Scriven EF. V, Ramsden C. Academic Press; Cambridge (MA, USA): 2015: 1-354
8b Lauder K, Toscani A, Scalacci N, Castagnolo D. Chem. Rev. 2017; 117: 14091
8c Lewis JC, Bergman RG, Ellman JA. Acc. Chem. Res. 2008; 41: 1013
8d Schultz DM, Wolfe JP. Synthesis 2012; 44: 351
8e Patil NT, Yamamoto Y. Chem. Rev. 2008; 108: 3395

9 Asymmetric Synthesis of Nitrogen Heterocycles. Royer J. Wiley-VCH; Weinheim: 2009

For selected examples, see:

10a Ohno H, Toda A, Miwa Y, Taga T, Osawa E, Yamaoka Y, Fujii N, Ibuka T. J. Org. Chem. 1999; 64: 2992
10b Dieter RK, Yu H. Org. Lett. 2001; 3: 3855
10c Billet M, Schoenfelder A, Klotz P, Mann A. Tetrahedron Lett. 2002; 43: 1453
10d Sai M, Matsubara S. Org. Lett. 2011; 13: 4676
10e Xu T, Mu X, Peng H, Liu G. Angew. Chem. Int. Ed. 2011; 50: 8176
10f Morita N, Krause N. Org. Lett. 2004; 6: 4121
10g Morita N, Krause N. Eur. J. Org. Chem. 2006; 4634
10h Kang S.-K, Kim K.-J. Org. Lett. 2001; 3: 511
10i Ma S, Yu F, Gao W. J. Org. Chem. 2003; 68: 5943

11 Ohno H, Kadoh Y, Fujii N, Tanaka T. Org. Lett. 2006; 8: 947
12 Wu P, Liu H, Tong X. Tetrahedron Lett. 2012; 53: 4673
13 Hayes CJ, Sherlock AE, Green MP, Wilson C, Blake AJ, Selby MD, Prodger JC. J. Org. Chem. 2008; 73: 2041
14 Tran G, Meier R, Harris L, Browne DL, Ley SV. J. Org. Chem. 2012; 77: 11071

15a Boomination SS. K, Hu W.-P, Sendi GP, Wang JJ. Adv. Synth. Catal. 2013; 355: 3570
15b Zheng C, Wang Y, Gan R. Org. Lett. 2015; 17: 916

16 Chogii I, Njardarson JT. Angew. Chem. Int. Ed. 2015; 54: 13706
17 Chelucci G, Saba A. Angew. Chem., Int. Ed. Engl. 1995; 34: 78
18 Duttwyler S, Lu C, Rheingold AL, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2012; 134: 4064

19a Beceño C, Krappitz T, Raabe G, Enders D. Synthesis 2015; 47: 38813
19b He L, Laurent G, Retailleau P, Folleas B, Brayer J.-L, Masson G. Angew. Chem. Int. Ed. 2013; 52: 11088
19c Tambar UK, Lee SK, Leighton JL. J. Am. Chem. Soc. 2010; 132: 10249

20 de la Pradilla RF, Simal C, Bates RH, Viso A, Infantes L. Org. Lett. 2013; 15: 4936

21a Zhu XF, Lan J, Kwon O. J. Am. Chem. Soc. 2003; 125: 4716
21b Zhou L, Yuan C, Zeng Y, Liu H, Wang C, Gao X, Wang Q, Zhang C, Guo H. Chem. Sci. 2018; 9: 1831

For selected examples, see:

22a Wang Z, Xu H, Su Q, Hu P, Shao P.-L, He Y, Lu Y. Org. Lett. 2017; 19: 3111
22b Hu P, Hu J, Jiao J, Tong X. Angew. Chem. Int. Ed. 2013; 52: 5319
22c Rutjes FP. J. T, Tjen KC. M. F, Wolf LB, Karstens WF. J, Schoemaker HE, Hiemstra H. Org. Lett. 1999; 1: 717
22d Inuki S, Iwata A, Oishi S, Fujii N, Ohno H. J. Org. Chem. 2011; 76: 2072
22e Ohno H, Mizutani T, Kadoh Y, Aso A, Miyamura K, Fujii N, Tanaka T. J. Org. Chem. 2007; 72: 4378
22f Inkui S, Oishi S, Fujii N, Ohno H. Org. Lett. 2008; 10: 5239

For examples, see:

23a Donohoe TJ, Guyo PM, Helliwell M. Tetrahedron Lett. 1999; 40: 435
23b Schafer A, Schafer B. Tetrahedron 1999; 55: 12309
23c Donohoe TJ, Thomas RE. Chem. Rec. 2007; 7: 180
23d Wu J, Tang W, Pettman A, Xiao J. Adv. Synth. Catal. 2013; 355: 35

For reviews, see:

24a Blechert S, Schuster M. Angew. Chem., Int. Ed. Engl. 1997; 36: 2036
24b Montgomery TP, Johns AM, Grubbs RH. Catalysts 2017; 6: 87
24c Ogba OM, Warner NC, O’Leary DJ, Grubbs RH. Chem. Soc. Rev. 2018; 47: 4510
24d Deiters A, Martin SF. Chem. Rev. 2004; 104: 2199

25a Fu GC, Grubbs RH. J. Am. Chem. Soc. 1992; 114: 5426
25b Fu GC, Grubbs RH. J. Am. Chem. Soc. 1992; 114: 7324

26a Ulman M, Grubbs RH. J. Org. Chem. 1999; 64: 7202
26b Yee NK, Farina V, Houpis IN, Haddad N, Frutos RP, Gallou F, Wang X.-j, Wei X, Simpson RD, Feng X, Fuchs V, Xu Y, Tan J, Zhang L, Xu J, Smith-Keenan LL, Vitous J, Ridges MD, Spinelli EM, Johnson M. J. Org. Chem. 2006; 71: 7133
26c Hong SH, Wenzel AG, Salguero TT, Day MW, Grubbs RH. J. Am. Chem. Soc. 2007; 129: 7961
26d Manzini S, Poater A, Nelson DJ, Cavallo L, Slawin AM. Z, Nolan SP. Angew. Chem. Int. Ed. 2014; 53: 8995
26e Wilson GO, Porter KA, Weissman H, White SR, Sottos NR, Moore JS. Adv. Synth. Catal. 2009; 351: 1817
26f Lummiss JA. M, Ireland BJ, Sommers JM, Fogg DE. ChemCatChem 2014; 6: 459
26g Ireland BJ, Dobigny BT, Fogg DE. ACS Catal. 2015; 5: 4690
26h Fu GC, Nguyen ST, Grubbs RH. J. Am. Chem. Soc. 1993; 115: 9856

27a Compain P. Adv. Synth. Catal. 2007; 349: 1829
27b Compain P, Hazelard D. Top. Heterocycl. Chem. 2017; 47: 111
27c Philips A. J, Abell A. D. Aldrichchim. Acta. 1999; 32: 75
27d Vernall A. J, Abell A. D. Aldrichchim. Acta. 2003; 36: 93
27e Felpin F.-X, Lebreton J. Eur. J. Org. Chem. 2003; 3693
27f Deiters A, Martin S. F. Chem. Rev. 2004; 104: 2199
27g Chattopadhyay S. K, Karmakar S, Majumdar K. C, Rahaman H, Roy B. Tetrahedron 2007; 63: 3919

28a Scholl M, Ding S, Lee CW, Grubbs RH. Org. Lett. 1999; 1: 953
28b Trnka TM, Morgan JP, Sanford MS, Wilhelm TE, School M, Choi TL, Ding S, Day MW, Grubbs RH. J. Am. Chem. Soc. 2003; 125: 2546

29 Zaidi K. Pharmacopeial Forum 2008; 34: 1345
30 Kuhn KM, Champagne TM, Hong SH, Wei W.-H, Nickel A, Lee CW, Virgil SC, Grubbs RH, Pederson RL. Org. Lett. 2010; 12: 984

31a Chao W, Weinreb SM. Org. Lett. 2003; 5: 2505
31b Chao W, Meketa ML, Weinreb SM. Synthesis 2004; 2058

For reviews of metal-catalyzed cross-couplings, see:

32a Metal-Catalyzed Cross-Coupling Reactions . de Meijere A, Diederich F. Wiley-VCH; Weinheim: 2004
32b Cross-Coupling Reactions: A Practical Guide. In Topics in Current Chemistry, Vol. 219. Miyaura N. Springer Verlag; New York: 2002
32c Handbook of Organopalladium Chemistry for Organic Synthesis. Negishi E.-i. Wiley-Interscience; New York: 2002

33 Gatti M, Drinkel E, Wu L, Pusteria I, Gaggia F, Dorta R. J. Am. Chem. Soc. 2010; 132: 15179

34a Fürstner A, Leitner A. Angew. Chem. Int. Ed. 2003; 42: 308
34b Fürstner A, Grabowski J, Lehmann CW. J. Org. Chem. 1999; 64: 8275
34c Scheiper B, Glorius F, Leitner A, Fürstner A. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 11960
34d Edwards AS, Wybrow RA, Johnstone C, Adams H, Harrity JP. Chem. Commun. 2002; 1542
34e Gracias V, Gasiecki AF, Moor JD, Akritopoulou-Zanze I, Djuric SW. Tetrahedron Lett. 2006; 47: 8977
34f Prusov E, Maier ME. Tetrahedron 2007; 63: 10486
34g Wright DL, Schulte JP. II, Page MA. Org. Lett. 2000; 2: 1847

35 Yang Q, Xiao WJ, Yu Z. Org. Lett. 2005; 7: 871
36 Woodward CP, Spiccia ND, Jackson WR, Robinson AJ. Chem. Commun. 2011; 47: 779

37a Boger DL, Turnbull P. J. Org. Chem. 1997; 62: 5849
37b Marten SF, Liao YS, Wong YL, Reing T. Tetrahedron Lett. 1994; 35: 691
37c Pilli RA, de Oliveira MD. C. F. Nat. Prod. Rep. 2000; 17: 117
37d Sakai R, Higa T. J. Am. Chem. Soc. 1986; 108: 6404
37e Wipf P, Spencer SR. J. Am. Chem. Soc. 2005; 127: 225

38 Teichert JF, Zhang S, van Zijl AW, Slaa JW, Minnaard AJ, Feringa BL. Org. Lett. 2010; 12: 4658

39a Garber SB, Kingsbury JS, Gray BL, Hoveyda AH. J. Am. Chem. Soc. 2000; 122: 8168
39b Gessler S, Randl S, Blechert S. Tetrahedron Lett. 2000; 41: 9973

40a Grela K, Harutyunyan S, Michrowska A. Angew. Chem. Int. Ed. 2002; 41: 4038
40b Grela K, Kim M. Eur. J. Org. Chem. 2003; 963
40c Van Veldhuizen JJ, Gillingham DG, Garber SB, Katoaka O, Hoveyda AH. J. Am. Chem. Soc. 2003; 125: 12502

41 Tzur E, Szadkowska A, Ben-Asuly A, Makal A, Goldberg I, Wozniak K, Grela K, Lemcoff NG. Chem. Eur. J. 2010; 16: 8726

42a Schmidt B. Angew. Chem. Int. Ed. 2003; 42: 4996
42b Yamamoto Y, Nakagai Y, Ohkoshi N, Itoh K. J. Am. Chem. Soc. 2001; 123: 6372
42c Hong S, Sanders DP, Lee CW, Grubbs RH. J. Am. Chem. Soc. 2005; 127: 17160

43a Slugovc C, Perner B, Stelzer F, Mereiter K. Organometallics 2004; 23: 3622
43b Burtscher D, Perner B, Mereiter K, Slugovc C. J. Organomet. Chem. 2006; 691: 5423

44a Ung T, Heijl A, Grubbs RH, Schrodi Y. Organometallics 2004; 23: 5399
44b Slugovc C, Burtscher D, Stelzer F, Mereiter K. Organometallics 2005; 24: 2255
44c Szadkowska A, Gstrein X, Burtscher D, Jarzembska K, Wozniak K, Slugovc C, Grela K. Organometallics 2010; 29: 117

45a Szadkowska A, Makal A, Wozniak K, Kadyrov R, Grela K. Organometallics 2009; 28: 2693
45b Kost T, Sigalov M, Goldberg I, Ben-Asuly A, Lemcoff NG. J. Organomet. Chem. 2008; 693: 2200
45c Ben-Asuly A, Tzur E, Diesendruck CE, Sigalov M, Goldberg I, Lemcoff NG. Organometallics 2008; 27: 811
45d Ben-Asuly A, Tzur E, Diesendruck CE, Sigalov M, Goldberg I, Lemcoff NG. Organometallics 2009; 28: 4652

46 Diesendruck CE, Tzur E, Ben-Asuly A, Goldberg I, Straub BF, Lemcoff NG. Inorg. Chem. 2009; 48: 10819
47 Lexer C, Burtscher D, Perner B, Tzur E, Lemcoff NG, Slugovc C. J. Organomet. Chem. 2011; 696: 2466
48 Kuethe J, Zhong Y.-L, Yasuda N, Beutner G, Linn K, Kim M, Marcune B, Dreher SD, Humphrey G, Pei T. Org. Lett. 2013; 15: 4174
49 Williams MJ, Kong J, Chung CK, Brunskill A, Campeau L.-C, McLaughlin M. Org. Lett. 2016; 18: 1952
50 Kajetanowicz A, Milewski M, Rogińska J, Gajda R, Woźniak K. Eur. J. Org. Chem. 2017; 626

51a Trnka TM, Grubbs RH. Acc. Chem. Res. 2001; 34: 18
51b Samojlowicz C, Bieniek M, Grela K. Chem. Rev. 2009; 109: 3708

52 Vougioukalakis GC, Grubbs RH. Chem. Rev. 2010; 110: 1746

53a Love JA, Morgan JP, Trnka TM, Grubbs RH. Angew. Chem. Int. Ed. 2002; 41: 4035
53b Clavier H, Petersen JL, Nolan SP. J. Organomet. Chem. 2006; 691: 54444

54a Boeda F, Clavier H, Nolan SP. Chem. Commun. 2008; 2726
54b Clavier H, Urbina-Blanco CA, Nolan SP. Organometallics 2009; 28: 2848
54c Bantriel X, Schmid TE, Randall RA. M, Slawin AM. Z, Xazin CS. J. Chem. Commun. 2010; 46: 7115
54d Clavier H, Nolan SP. Chem. Eur. J. 2007; 13: 8029
54e Bieniek M, Michrowska A, Usanov DL, Grela K. Chem. Eur. J. 2008; 14: 806

55 Urbina-Blanco CA, Leitgeb A, Slugovc C, Bantreil X, Clavier H, Slawin AM. Z, Nolan SP. Chem. Eur. J. 2011; 17: 5045
56 Manzini S, Urbina Blanco CA, Slawin AM. Z, Nolan SP. Organometallics 2012; 31: 6514

57a Vehlow K, Gessler S, Blechert S. Angew. Chem. Int. Ed. 2007; 46: 8082
57b Hong SH, Chlenov A, Day MW, Grubbs RH. Angew. Chem. Int. Ed. 2007; 46: 5184

58a Chung CK, Grubbs RH. Org. Lett. 2008; 10: 2693
58b Kuhn KM, Bourg J.-B, Chung CK, Virgil SC, Grubbs RH. J. Am. Chem. Soc. 2009; 131: 5313
58c Grisi F, Mariconda A, Costabile C, Bertolasi V, Longo P. Organometallics 2009; 28: 4988
58d Costabile C, Mariconda A, Cavallo L, Longo P, Bertolasi V, Ragone F, Grisi F. Chem. Eur. J. 2011; 17: 8618

59 Torborg C, Szczepaniak G, Zielinski A, Malinska M, Wozniak K, Grela K. Chem. Commun. 2013; 49: 3188

60a Furstner A, Liebl M, Lehmann CW, Picquet M, Kunz R, Bruneau C, Touchard D, Dixneuf PH. Chem. Eur. J. 2000; 6: 1847
60b Miyaki Y, Onishi T, Kurosawa H. Inorg. Chim. Acta 2000; 300–302: 369
60c Wang D, Wurst K, Knolle W, Decker U, Prager L, Naumov S, Buchmeiser MR. Angew. Chem. Int. Ed. 2008; 47: 3267
60d Volland MA. O, Hansen SM, Rominger F, Hofmann P. Organometallics 2004; 23: 800
60e Zirngast M, Pump E, Leitgeb A, Albering JH, Slugovc C. Chem. Commun. 2011; 47: 2261

61a Songis O, Slawin AM. Z, Cazin CS. J. Chem. Commun. 2012; 48: 1266
61b Volland MA. O, Hansen SM, Rominger F, Hofmann P. Organometallics 2004; 23: 800

62 Olefin Metathesis: Theory and Practice . Grela K. Wiley-VCH; Weinheim: 2014
63 For examples, see: Alexander JB, La DS, Cefalo DR, Hoveyda AH, Schrock RR. J. Am. Chem. Soc. 1998; 120: 4041

64a La DS, Alexander JB, Cefalo DR, Graf DD, Hoveyda AH, Schrock RR. J. Am. Chem. Soc. 1998; 120: 9720
64b Zhu SS, Cefalo DR, La DS, Jamieson JY, Davis WM, Hoveyda AH, Schrock RR. J. Am. Chem. Soc. 1999; 121: 8251
64c Cefalo DR, Kiely AF, Wuchrer M, Jamieson JY, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2001; 123: 3139
64d Keily AF, Jernelius JA, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2002; 124: 2868
64e Sattely ES, Cortez A, Moebius DC, Schrock RR, Hoveyda AH. J. Am. Chem. Soc. 2005; 127: 8526

65 Dolman SJ, Satterly ES, Hoveyda AH, Schrock RR. J. Am. Chem. Soc. 2002; 124: 6991
66 Hartung J, Dornan PK, Grubbs RH. J. Am. Chem. Soc. 2014; 136: 13029
67 Costabile C, Cavallo L. J. Am. Chem. Soc. 2004; 126: 9592
68 Paradiso V, Bertolasi V, Costabile C, Caruso T, Dąbrowski M, Grela K, Grisi F. Organometallics 2017; 36: 3692
69 Paradiso V, Bertolasi V, Costabile C, Grisi F. Dalton Trans. 2016; 45: 561
70 Fu GC, Grubbs RH. J. Am. Chem. Soc. 1993; 115: 3800
71 Zhou J, Rainier JD. Org. Lett. 2009; 11: 3774

72a This work was first reported as Ludwig, J. R.; Gianino, J. B.; Schindler, C., Abstracts of Papers, 250th National Meeting of the American Chemical Society, Boston MA, Aug 16–20, 2015; American Chemical Society: Washington DC, 2015, ORGN-388. Nitrogen-containing substrates were disclosed as challenging for Lewis acid catalyzed carbonyl-olefin metathesis proceeding in 37% yield.
72b Ludwig JR, Zimmerman PM, Gianino JB, Schindler CS. Nature (London) 2016; 533: 374
72c Ludwig JR, Phan S, McAtee CC, Zimmerman PM, Devery JJ. III, Schindler CS. J. Am. Chem. Soc. 2017; 139: 10832

73 Ma L, Li W, Xi H, Bai X, Ma E, Yan X, Li Z. Angew. Chem. Int. Ed. 2016; 55: 10410
74 Groso EJ, Golonka AN, Harding RA, Alexander BW, Sodano TM, Schindler CS. ACS Catal. 2018; 8: 2006
75 Groso E. J., Schindler C. S.; Org. Lett.; manuscript in revision.