1.4 Metal-Catalyzed Intramolecular Cyclizations Involving Cyclopropane and Cyclopropene Ring Opening

X.-Y. Tang; M. Shi

doi:10.1055/sos-SD-221-00093

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Gao, S. et al.: 2016 Science of Synthesis, 2016/4a: Metal-Catalyzed Cyclization Reactions 1 DOI: 10.1055/sos-SD-221-00093

Metal-Catalyzed Cyclization Reactions 1

1.4 Metal-Catalyzed Intramolecular Cyclizations Involving Cyclopropane and Cyclopropene Ring Opening

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Editors: Gao, S.; Ma, S.

Authors: Alderson, J.; Beccalli, E. M.; Bonetti, A.; Gao, S.; Guiry, P.; Jammi, S.; Mazza, A.; Nottingham, C.; Phelps, A.; Schomaker, J. M.; Shi, M.; Tang, X.-Y.; Wang, D.; Yamamoto, Y.; You, S. ; Zhang, L.; Zhang, X.

Title: Metal-Catalyzed Cyclization Reactions 1

Print ISBN: 9783131998613; Online ISBN: 9783132403406; Book DOI: 10.1055/b-003-129294

1st edition © 2016 Georg Thieme Verlag KG
Georg Thieme Verlag, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries

Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Koch, G.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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X.-Y. Tang; M. Shi

Abstract

Due to the ring strain of cyclopropane rings, transition-metal catalysts can easily undergo an oxidative addition with the cyclopropane moiety of methylenecyclopropanes (MCPs) to give trimethylenemethane (TMM) intermediates. Subsequent intramolecular cyclization with unsaturated systems takes place to give cyclized products. Moreover, in the presence of a chiral ligand, high enantioselectivity can be achieved. The ring-fused products are versatile building blocks in organic synthesis.

Key words

cyclopropanes - methylenecyclopropanes - ring-opening reactions - cyclization - alkenes - alkynes - transition-metal catalysts - trimethylenemethanes - palladium - nickel - rhodium - ruthenium - chiral synthesis

1 Ma S, Lu L, Zhang J. J. Am. Chem. Soc. 2004; 126: 9645

PubMed Search in Google Scholar

2 Siriwardana AI, Kamada M, Nakamura I, Yamamoto Y. J. Org. Chem. 2005; 70: 5932

PubMed Search in Google Scholar

3 Delgado A, Rodrígues JR, Castedo L, Mascareñas JL. J. Am. Chem. Soc. 2003; 125: 9282

PubMed Search in Google Scholar

4 López F, Delgado A, Rodrígues JR, Castedo L, Mascareñas JL. J. Am. Chem. Soc. 2004; 126: 10262

PubMed Search in Google Scholar

5 Gulías M, Durán J, López F, Castedo L, Mascareñas JL. J. Am. Chem. Soc. 2007; 129: 11026

PubMed Search in Google Scholar

6 Shi M, Liu L.-P, Tang J. J. Am. Chem. Soc. 2006; 128: 7430

PubMed Search in Google Scholar

7 Tian G.-Q, Yuan Z.-L, Zhu Z.-B, Shi M. Chem. Commun. (Cambridge) 2008; 2668

PubMed

8 Fürstner A, Aïssa C. J. Am. Chem. Soc. 2006; 128: 6306

PubMed Search in Google Scholar

9 Zhang D.-H, Tang X.-Y, Wei Y, Shi M. Chem.–Eur. J. 2013; 19: 13668

PubMed Search in Google Scholar

10 Aïssa C, Fürstner A. J. Am. Chem. Soc. 2007; 129: 14836

PubMed Search in Google Scholar

11 Chen K, Zhu Z.-Z, Tang X.-Y, Shi M. Angew. Chem. Int. Ed. 2014; 53: 6645

PubMed Search in Google Scholar

12 Yao B, Li Y, Liang Z, Zhang Y. Org. Lett. 2011; 13: 640

PubMed Search in Google Scholar

13 Li S, Luo Y, Wu J. Org. Lett. 2011; 13: 3190

PubMed Search in Google Scholar

14 Scott ME, Bethuel Y, Lautens M. J. Am. Chem. Soc. 2007; 129: 1482

PubMed Search in Google Scholar

15 Sethofer SG, Staben ST, Hung OY, Toste FD. Org. Lett. 2008; 10: 4315

PubMed Search in Google Scholar

16 Yao L.-F, Wei Y, Shi M. J. Org. Chem. 2009; 74: 9466

PubMed Search in Google Scholar

17 Felix RJ, Gutierrez O, Tantillo DJ, Gagné MR. J. Org. Chem. 2013; 78: 5685

PubMed Search in Google Scholar

18 Zheng H, Adduci LL, Felix RJ, Gagné MR. Angew. Chem. Int. Ed. 2014; 53: 7904

PubMed Search in Google Scholar

19 Zhang D.-H, Du K, Shi M. Org. Biomol. Chem. 2012; 10: 3763

PubMed Search in Google Scholar

20 Zriba R, Gandon V, Aubert C, Fensterbank L, Malacria M. Chem.–Eur. J. 2008; 14: 1482

PubMed Search in Google Scholar

21 Jackson SK, Karadeolian A, Driega AB, Kerr MA. J. Am. Chem. Soc. 2008; 130: 4196

PubMed Search in Google Scholar

22 Dias DA, Kerr MA. Org. Lett. 2009; 11: 3694

PubMed Search in Google Scholar

23 Xing S, Pan W, Liu C, Ren J, Wang Z. Angew. Chem. Int. Ed. 2010; 49: 3215

PubMed Search in Google Scholar

24 Beal RB, Dombroski MA, Snider BB. J. Org. Chem. 1986; 51: 4391

Search in Google Scholar

25 Xing S, Li Y, Li Z, Liu C, Ren J, Wang Z. Angew. Chem. Int. Ed. 2011; 50: 12605

PubMed Search in Google Scholar

26 Zhu W, Fang J, Liu Y, Wang Z. Angew. Chem. Int. Ed. 2013; 52: 2032

PubMed Search in Google Scholar

27 Wang Z, Ren J, Wang Z. Org. Lett. 2013; 15: 5682

PubMed Search in Google Scholar

28 Xia X.-F, Song X.-R, Liu X.-Y, Liang Y.-M. Chem.–Asian J. 2012; 7: 1538

PubMed Search in Google Scholar

29 Patil DV, Phun LH, France S. Org. Lett. 2010; 12: 5684

PubMed Search in Google Scholar

30 Aponte-Guzmán JA, Taylor JE, Tillman JE, France S. Org. Lett. 2014; 16: 3788

PubMed Search in Google Scholar

31 Patil DV, Cavitt MA, Grzybowski P, France S. Chem. Commun. (Cambridge) 2011; 47: 10278

PubMed Search in Google Scholar

32 Brand C, Rauch G, Zanoni M, Dittrich B, Werz DB. J. Org. Chem. 2009; 74: 8779

PubMed Search in Google Scholar

33 Zhang G, Huang X, Li G, Zhang L. J. Am. Chem. Soc. 2008; 130: 1814

PubMed Search in Google Scholar

34 Bai Y, Tao W, Ren J, Wang Z. Angew. Chem. Int. Ed. 2012; 51: 4112

PubMed Search in Google Scholar

35 Zhu J, Liang Y, Wang L, Zheng Z.-B, Houk KN, Tang Y. J. Am. Chem. Soc. 2014; 136: 6900

PubMed Search in Google Scholar

36 Fisher EL, Wilkerson-Hill SM, Sarpong R. J. Am. Chem. Soc. 2012; 134: 9946

PubMed Search in Google Scholar

37 Xu G.-C, Liu L.-P, Lu J.-M, Shi M. J. Am. Chem. Soc. 2005; 127: 14552

PubMed Search in Google Scholar

38 Shi M, Wu L, Lu J.-M. J. Org. Chem. 2008; 73: 8344

PubMed Search in Google Scholar

39 Li W, Yuan W, Pindi S, Shi M, Li G. Org. Lett. 2010; 12: 920

PubMed Search in Google Scholar

40 Lu B.-L, Wei Y, Shi M. Chem.–Eur. J. 2010; 16: 10975

PubMed Search in Google Scholar

41 Wu L, Shi M. Chem.–Eur. J. 2011; 17: 13160

PubMed Search in Google Scholar

42 Yuan W, Tang X.-Y, Wei Y, Shi M. Chem.–Eur. J. 2014; 20: 3198

PubMed Search in Google Scholar

43 Huang X, Su C, Liu Q, Song Y. Synlett 2008; 229

44 Lu B.-L, Shi M. Angew. Chem. Int. Ed. 2011; 50: 12027

PubMed Search in Google Scholar

45 Miao M, Cao J, Zhang J, Huang X, Wu L. J. Org. Chem. 2013; 78: 2687

PubMed Search in Google Scholar

46 Miao M, Cao J, Zhang J, Huang X, Wu L. Org. Lett. 2012; 14: 2718

PubMed Search in Google Scholar

47 Iwasawa N, Matsuo T, Iwamoto M, Ikeno T. J. Am. Chem. Soc. 1998; 120: 3903

Search in Google Scholar

48 Markham JP, Staben ST, Toste FD. J. Am. Chem. Soc. 2005; 127: 9708

PubMed Search in Google Scholar

49 Barluenga J, Tudela E, Vicente R, Ballesteros A, Tomás M. Angew. Chem. Int. Ed. 2011; 50: 2107

PubMed Search in Google Scholar

50 Zhang Z, Tang X.-Y, Xu Q, Shi M. Chem.–Eur. J. 2013; 19: 10625

PubMed Search in Google Scholar

51 Chen A, Lin R, Liu Q, Jiao N. Chem. Commun. (Cambridge) 2009; 6842

PubMed

52 Trost BM, Xie J, Maulide N. J. Am. Chem. Soc. 2008; 130: 17258

PubMed Search in Google Scholar

53 Chen G, Zhang X.-N, Wei Y, Tang X.-Y, Shi M. Angew. Chem. Int. Ed. 2014; 53: 8492

PubMed Search in Google Scholar

54 Lu Z, Shen M, Yoon TP. J. Am. Chem. Soc. 2011; 133: 1162

PubMed Search in Google Scholar

55 Tsuritani T, Yamamoto Y, Kawasaki M, Mase T. Org. Lett. 2009; 11: 1043

PubMed Search in Google Scholar

56 Liu L, Zhang J. Angew. Chem. Int. Ed. 2009; 48: 6093

PubMed Search in Google Scholar

57 Xu H, Zhang W, Shu D, Werness JB, Tang W. Angew. Chem. Int. Ed. 2008; 47: 8933

PubMed Search in Google Scholar

58 Liu R, Zhang M, Winston-McPherson G, Tang W. Chem. Commun. (Cambridge) 2013; 49: 4376

PubMed Search in Google Scholar

59 Tomilov Yu. V, Shapiro EA, Protopopova MN, Ioffe AI, Dolgii IE, Nefedov OM. Izv. Akad. Nauk SSSR, Ser. Khim. 1985; 631 Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1985; 34: 576

Search in Google Scholar

60 Davies HML, Romines KR. Tetrahedron 1988; 44: 3343

Search in Google Scholar

61 Padwa A, Kassir JM, Xu SL. J. Org. Chem. 1991; 56: 6971

Search in Google Scholar

62 Müller P, Pautex N, Doyle MP, Bagheri V. Helv. Chim. Acta. 1990; 73: 1233

Search in Google Scholar

63 Padwa A, Chiacchio U, Garreau Y, Kassir JM, Krumpe KE, Schoffstall AM. J. Org. Chem. 1990; 55: 414

Search in Google Scholar

64 Padwa A, Straub CS. Org. Lett. 2000; 2: 2093

PubMed Search in Google Scholar

65 Chuprakov S, Gevorgyan V. Org. Lett. 2007; 9: 4463

PubMed Search in Google Scholar

66 Archambeau A, Meige F, Meyer C, Cossy J. Angew. Chem. Int. Ed. 2012; 51: 11540

PubMed Search in Google Scholar

67 Zhang H, Li C, Xie G, Wang B, Zhang Y, Wang J. J. Org. Chem. 2014; 79: 6286

PubMed Search in Google Scholar

68 Chen J, Ma S. Chem.–Asian J. 2010; 5: 2415

PubMed Search in Google Scholar

69 Ma S, Zhang J. J. Am. Chem. Soc. 2003; 125: 12386

PubMed Search in Google Scholar

70 Shao L.-X, Zhang Y.-P, Qi M.-H, Shi M. Org. Lett. 2007; 9: 117

PubMed Search in Google Scholar

71 Zhu Z.-B, Shi M. Chem.–Eur. J. 2008; 14: 10219

PubMed Search in Google Scholar

72 Miege F, Meyer C, Cossy J. Org. Lett. 2010; 12: 4144

PubMed Search in Google Scholar

73 Miege F, Meyer C, Cossy J. Chem.–Eur. J. 2012; 18: 7810

PubMed Search in Google Scholar

74 Li C, Zeng Y, Wang J. Tetrahedron Lett. 2009; 50: 2956

Search in Google Scholar

75 Li C, Zeng Y, Zhang H, Fang J, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2010; 49: 6413

PubMed Search in Google Scholar

76 Evans PA, Inglesby PA. J. Am. Chem. Soc. 2012; 134: 3635

PubMed Search in Google Scholar

77 Jung ME, Chang JJ. Org. Lett. 2010; 12: 2962

PubMed Search in Google Scholar

78 Heathcock CH, Blumenkopf TA, Smith KM. J. Org. Chem. 1989; 54: 1548

Search in Google Scholar

79 Zhang M, Huang X, Shen L, Qin Y. J. Am. Chem. Soc. 2009; 131: 6013

PubMed Search in Google Scholar

80 Liu R, Zhang M, Wyche TP, Winston-McPherson GN, Bugni TS, Tang W. Angew. Chem. Int. Ed. 2012; 51: 7503

PubMed Search in Google Scholar