From Straightforward Gold(I)-Catalyzed Enyne Cyclizations to more Demanding Intermolecular Reactions of Alkynes with Alkenes

Cristina García-Morales; Antonio M. Echavarren

doi:10.1055/s-0037-1610203

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(17): 2225-2237
DOI: 10.1055/s-0037-1610203

account

From Straightforward Gold(I)-Catalyzed Enyne Cyclizations to more Demanding Intermolecular Reactions of Alkynes with Alkenes

Cristina García-Morales

^aInstitute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain eMail: aechavarren@iciq.es

^bDepartament de Química Orgànica i Analítica, Universitat Rovira i Virgili, C/ Marcel·lí Domingo s/n, 43007 Tarragona, Spain

,

Antonio M. Echavarren*

^aInstitute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain eMail: aechavarren@iciq.es

^bDepartament de Química Orgànica i Analítica, Universitat Rovira i Virgili, C/ Marcel·lí Domingo s/n, 43007 Tarragona, Spain

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Gold(I) complexes are the catalysts of choice for the selective activation of alkynes in the presence of other unsaturated functional groups. In this Account, we present the development of gold(I)-catalyzed intermolecular reactions of terminal alkynes with functionalized alkenes. In particular, we focus on the synthesis of cyclobutenes by asymmetric gold(I)-catalyzed [2+2] cycloaddition and its applications.

1 Introduction

2 Intramolecular Gold(I)-Catalyzed Synthesis of Cyclobutenes

2.1 Role of Cyclobutenes in 1,n-Enynes Cycloisomerizations

2.2 [2+2] Cycloaddition of 1,n-Enynes

3 Intermolecular Gold(I)-Catalyzed Reactions of Terminal Alkynes with Alkenes

3.1 [2+2] Cycloaddition of Alkynes with Alkenes

3.2 Reactions of Propiolic Acid with Alkenes

3.3 [2+2+2] Cycloaddition of Alkynes with Oxoalkenes

3.4 Reaction of Alkynes with Furanes

4 Gold(I)-Catalyzed Enantioselective Synthesis of Cyclobutenes

5 Concluding Remarks

Key words

gold - alkynes - alkenes - cycloaddition - cyclobutenes - asymmetric catalysis

Volltext

Referenzen

References

1a Fürstner A. Chem. Soc. Rev. 2009; 38: 3208
1b Shapiro ND. Toste FD. Synlett 2010; 675
1c Obradors C. Echavarren AM. Acc. Chem. Res. 2014; 47: 902
1d Fensterbank L. Malacria M. Acc. Chem. Res. 2014; 47: 953
1e Dorel R. Echavarren AM. Chem. Rev. 2015; 115: 9028
1f Pflästerer D. Hashmi AS. K. Chem. Soc. Rev. 2016; 45: 1331
1g Echavarren AM. Muratore MN. López-Carrillo V. Escribano-Cuesta A. Huguet A. Obradors C. Org. React. . 2017. Vol. 92: Chap 1

2 Teles JH. Brode S. Chabanas M. Angew. Chem. Int. Ed. 1998; 37: 1415
3 Mizushima E. Sato K. Hayashi T. Tanaka M. Angew. Chem. Int. Ed. 2002; 41: 4563
4 Hashmi AS. K. Frost TM. Bats JW. J. Am. Chem. Soc. 2000; 122: 11553

5a Brown TJ. Dickens MG. Widenhoefer RA. J. Am. Chem. Soc. 2009; 131: 6350
5b Brown TJ. Dickens MG. Widenhoefer RA. Chem. Commun. 2009; 6451
5c Brown TJ. Widenhoefer RA. J. Organomet. Chem. 2011; 696: 1216
5d Brooner RE. M. Widenhoefer RA. Angew. Chem. Int. Ed. 2013; 52: 11714

6 Urbano J. Hormigo AJ. de Frémont P. Nolan PS. Díaz-Requejo MM. Pérez PJ. Chem. Commun. 2008; 759
7 Muratore ME. Homs A. Obradors C. Echavarren AM. Chem. Asian. J. 2014; 9: 3066

8a Widenhoefer RA. Chem. Eur. J. 2008; 14: 5382
8b Sengupta S. Shi X. ChemCatChem 2010; 2: 609
8c Pradal A. Toullec PY. Michelet V. Synthesis 2011; 1501
8d Wang YM. Lackner AD. Toste FD. Acc. Chem. Res. 2014; 47: 889
8e Zi W. Toste FD. Chem. Soc. Rev. 2016; 45: 4567
8f Li Y. Li W. Zhang J. Chem. Eur. J. 2017; 23: 467

9a Hamilton GL. Kang EJ. Mba M. Toste FD. Science 2007; 317: 496
9b Aikawa K. Kojima M. Mikami K. Angew. Chem. Int. Ed. 2009; 48: 6073
9c Aikawa K. Kojima M. Mikami K. Adv. Synth. Catal. 2010; 352: 3131
9d Tu X. Gong L. Angew. Chem. Int. Ed. 2012; 51: 11346

10a Francos J. Grande-Carmona F. Faustino H. Iglesias-Sigüenza J. Díez E. Alonso I. Fernández R. Lassaletta JM. López F. Ujaque G. Chem. Eur. J. 2013; 19: 15248
10b Suárez-Pantiga S. Hernández-Díaz C. Rubio E. González JM. Angew. Chem. Int. Ed. 2012; 51: 11552
10c Li GH. Zhou W. Li W. Bi QW. Wang Z. Zhao GZ. Hu WX. Chen Z. Chem. Commun. 2013; 49: 4770
10d Varela I. Faustino H. Díez E. Iglesias-Sigüenza J. Grande-Carmona F. Fernández R. Lassaletta JM. Mascareñas JL. López F. ACS Catal. 2017; 7: 2397

Leading references:

11a Snyder SA. Tang Z.-Y. Gupta R. J. Am. Chem. Soc. 2009; 131: 5744
11b Denmark SE. Jaunet A. J. Am. Chem. Soc. 2013; 135: 6419
11c Denmark SE. Hartmann E. Kornfilt DJ. P. Wang H. Nat. Chem. 2014; 6: 1056
11d Denmark SE. Carson N. Org. Lett. 2015; 17: 5728
11e Cresswell AJ. Eey ST.-C. Denmark SE. Angew. Chem. Int. Ed. 2015; 54: 15642
11f Hu DX. Seidl FJ. Bucher C. Burns NZ. J. Am. Chem. Soc. 2015; 137: 3795
11g Landry ML. Hu DX. McKenna GM. Burns NZ. J. Am. Chem. Soc. 2016; 138: 5150
11h Denmark SE. Ryabchuk P. Burk MT. Gilbert BB. J. Org. Chem. 2016; 81: 10411
11i Samanta RS. Yamamoto H. J. Am. Chem. Soc. 2017; 139: 1460

12 Nieto-Oberhuber C. Muñoz MP. Buñuel E. Nevado C. Cárdenas DJ. Echavarren AM. Angew. Chem. Int. Ed. 2004; 43: 2402
13 Nieto-Oberhuber C. López S. Muñoz MP. Cárdenas DJ. Buñuel E. Nevado C. Echavarren AM. Angew. Chem. Int. Ed. 2005; 44: 6146
14 Escribano-Cuesta A. Pérez-Galán P. Herrero-Gómez E. Sekine M. Braga AA. C. Maseras F. Echavarren AM. Org. Biomol. Chem. 2012; 10: 6105

15a Hashmi AS. K. Angew. Chem. Int. Ed. 2008; 47: 6754
15b Cianleoni G. Biasiolo L. Bistoni G. Macchioni A. Tarantelli F. Zuccaccia D. Belpassi L. Chem. Eur. J. 2015; 21: 2467

16a Benitez D. Shapiro ND. Tkatchouk E. Wang Y. Goddard WA. III. Toste D. F. 2009; 1: 482
16b Echavarren AM. Nat. Chem. 2009; 1: 431

17a Wang Y. Muratore ME. Echavarren AM. Chem. Eur. J. 2015; 21: 7332
17b Caballero A. Pérez PJ. Chem. Eur. J. 2017; 58: 14389

18a Steinborn D. Beckea S. Herzoga R. Günter M. Kircheisen R. Stoeckli-Evans H. Bruhn C. Z. Anorg. Allg. Chem. 1968; 624: 1303
18b Nesmeyanov AN. Perevalova EG. Smyslova EI. Dyadchenko VP. Grandberg KI. Izv. Akad. Nauk SSSR, Ser. Khim. 1977; 2610

19 Sarria Toro JM. García-Morales C. Raducan M. Smirnova ES. Echavarren AM. Angew. Chem. Int. Ed. 2017; 56: 1859
20 Nieto-Oberhuber C. López S. Echavarren AM. J. Am. Chem. Soc. 2005; 127: 6178
21 Nieto-Oberhuber C. Pérez-Galán P. Herrero-Gómez E. Lauterbach T. Rodríguez C. López S. Bour C. Rosellón A. Cárdenas DJ. Echavarren AM. J. Am. Chem. Soc. 2008; 130: 269

22a Brooner RE. M. Brown TJ. Widenhoefer RA. Angew. Chem. Int. Ed. 2013; 52: 1
22b Brooner RE. M. Robertson BD. Widenhoefer RA. Organometallics 2014; 33: 6466

23 Kim N. Brooner RE. M. Widenhoefer RA. Organometallics 2017; 36: 673
24 Odabachian Y. Gagosz F. Adv. Synth. Catal. 2009; 351: 379
25 Inagaki F. Matsumoto C. Okada Y. Maruyama N. Mukai C. Angew. Chem. Int. Ed. 2015; 54: 818
26 Iwai T. Ueno M. Okochi H. Sawamura M. Adv. Synth. Catal. 2018; 360: 670
27 Obradors C. Leboeuf D. Aydin J. Echavarren AM. Org. Lett. 2013; 15: 1576
28 Homs A. Obradors C. Leboeuf D. Echavarren AM. Adv. Synth. Catal. 2014; 356: 221
29 Ranieri B. Obradors C. Mato M. Echavarren AM. Org. Lett. 2016; 18: 1614
30 López-Carrillo V. Echavarren AM. J. Am. Chem. Soc. 2010; 132: 9292

31a Wei C. Li CJ. J. Am. Chem. Soc. 2003; 125: 9584
31b Lavallo V. Frey GD. Kousar S. Donna-dieu B. Bertrand G. Proc. Natl. Acad. Sci. U.S.A. 2007; 104: 13569
31c Hooper TN. Green M. Russell CA. Chem. Commun. 2010; 46: 2313
31d Simonneau A. Jaroschik F. Lesage D. Karanik M. Guillot R. Malacria M. Tabet J.-C. Goddard J.-P. Fensterbank L. Gandon V. Gimbert Y. Chem. Sci. 2011; 2: 2417
31e Grirrane A. Garcia H. Corma A. Alvarez E. ACS Catal. 2011; 1: 1647
31f Brown TJ. Widenhoefer RA. Organometallics 2011; 30: 6003
31g Raducan M. Moreno M. Bour C. Echavarren AM. Chem. Commun. 2012; 48: 52
31h Gómez-Suárez A. Dupuis S. Slawin AM. Z. Nolan SP. Angew. Chem. Int. Ed. 2013; 52: 938; Angew. Chem. 2013, 125, 972

32a Ye L. Wang Y. Aue DH. Zhang L. J. Am. Chem. Soc. 2012; 134: 31
32b Hashmi AS. K. Braun I. Rudolph M. Rominger F. Organometallics 2012; 31: 644
32c Hashmi AS. K. Lauterbach T. Nösel P. Vilhelmsen MH. Rudolph M. Rominger F. Chem. Eur. J. 2013; 19: 1058
32d Hashmi AS. K. Wieteck M. Braun I. Nösel P. Jongbloed L. Rudolph M. Rominger M. Adv. Synth. Catal. 2012; 354: 555
32e Hansmann MM. Rudolph M. Rominger F. Hashmi AS. K. Angew. Chem. Int. Ed. 2013; 52: 2593
32f Wang Y. Yepremyan A. Ghorai S. Todd R. Aue DH. Zhang L. Angew. Chem. Int. Ed. 2013; 52: 7795
32g Larsen MH. Houk KN. Hashmi AS. K. J. Am. Chem. Soc. 2015; 137: 10668
32h Asiri AM. Hashmi AS. K. Hashmi AS. K. Chem. Soc. Rev. 2016; 45: 4471

33a Cheong PH.-Y. Morganelli P. Luzung MR. Houk KN. Toste FD. J. Am. Chem. Soc. 2008; 130: 4517
33b Jaroschik F. Simonneau A. Lemière G. Cariou K. Agenet N. Amouri H. Aubert C. Goddard J.-P. Lesage D. Malacria M. Gimbert Y. Gandon V. Fensterbank L. ACS Catal. 2016; 6: 5146

34 Ferrer S. Echavarren AM. Organometallics 2018; 37: 781
35 de Orbe ME. Amenós L. Kirillova MS. Wang Y. López-Carrillo V. Maseras F. Echavarren AM. J. Am. Chem. Soc. 2017; 139: 10302
36 de Orbe M. E., Echavarren A. M.; Eur. J. Org. Chem.; 2018, in press; DOI: 10.1002/ejoc.201800170.
37 Bai Y. Luo Z. Wang Y. Gao J. Zhang L. J. Am. Chem. Soc. 2018; 140: 5860
38 Yeom H.-S. Koo J. Park H.-S. Wang Y. Liang Y. Yu Z.-X. Shin S. J. Am. Chem. Soc. 2012; 134: 208
39 Jiménez-Núñez E. Claverie CK. Nieto-Oberhuber C. Echavarren AM. Angew. Chem. Int. Ed. 2006; 45: 5452
40 Jiménez-Núñez E. Molawi K. Echavarren AM. Chem. Commun. 2009; 7327
41 Molawi K. Delpont N. Echavarren AM. Angew. Chem. Int. Ed. 2010; 49: 3517
42 Obradors C. Echavarren AM. Chem. Eur. J. 2013; 19: 3547

43a Hashmi AS. K. Rudolph M. Weyrauch JP. Wölfle M. Frey W. Bats W. Angew. Chem. Int. Ed. 2005; 44: 2798 ; Angew. Chem. 2005, 117, 2858
43b Hashmi AS. K. Blanco MC. Eur. J. Org. Chem. 2006; 4340
43c Hashmi AS. K. Salathé R. Frey W. Chem. Eur. J. 2006; 12: 6991
43d Hashmi AS. K. Kurpejovic E. Wölfle M. Frey W. Bats JW. Adv. Synth. Catal. 2007; 349: 1743
43e Hashmi AS. K. Rudolph M. Siehl H.-U. Tanaka M. Bats JW. Frey W. Chem. Eur. J. 2008; 14: 3703
43f Hashmi AS. K. Hofmann J. Shi S. Schütz A. Rudolph M. Lothschütz C. Wieteck M. Bührle M. Wölfle M. Rominger F. Chem. Eur. J. 2013; 19: 382

44 Huguet N. Leboeuf D. Echavarren AM. Chem. Eur. J. 2013; 19: 6581

45a Lee-Ruff E. Mladenova G. Chem. Rev. 2003; 103: 1449
45b Namyslo JC. Kaufmann DE. Chem. Rev. 2003; 103: 1485
45c Misale A. Niyomchon S. Maulide N. Acc. Chem. Res. 2016; 49: 2444

46a Masarwa A. Fürstner A. Marek I. Chem. Commun. 2009; 5760
46b Liu R. Zhang M. Wyche TP. Winston-McPherson GN. Bugni TS. Tang W. Angew. Chem. Int. Ed. 2012; 51: 7503
46c Niyomchon S. Audisio D. Luparia M. Maulide N. Org. Lett. 2013; 15: 2318
46d Souris C. Misale A. Chen Y. Luparia M. Maulide N. Org. Lett. 2015; 17: 4486
46e Chen Y.-J. Hu T.-J. Feng C.-G. Lin G.-Q. Chem. Commun. 2015; 51: 8773
46f Eisold M. Didier D. Angew. Chem. Int. Ed. 2015; 54: 15884
46g Guisán-Ceinos M. Parra A. Martín-Heras V. Tortosa M. Angew. Chem. Int. Ed. 2016; 128: 7083
46h Roy SR. Eijsberg H. Bruffaerts J. Marek I. Chem. Sci. 2016; 8: 334
46i Eisold M. Baumann AN. Kiefl GM. Emmerling ST. Didier D. Chem. Eur. J. 2016; 23: 1634
46j Baumann AN. Eisold M. Didier D. Org. Lett. 2017; 19: 2114

47a Collado IG. Hanson JR. Macías-Sánchez AJ. Nat. Prod. Rep. 1998; 15: 187
47b Wessjohann LA. Brandt W. Thiemann T. Chem. Rev. 2003; 103: 1625
47c Dembitsky VM. J. Nat. Med. 2008; 62: 1
47d Xu Y. Conner ML. Brown MK. Angew. Chem. Int. Ed. 2015; 54: 11918

48a Grongsaard P. Bulger PG. Wallace DJ. Tan L. Chen Q. Dolman SJ. Nyrop J. Hoerrner RS. Weisel M. Arredondo J. Itoh T. Xie C. Wen X. Zhao D. Muzzio DJ. Bassan EM. Shultz CS. Org. Process Res. Dev. 2012; 16: 1069
48b Lukin K. Kishore V. Gordon T. Org. Process Res. Dev. 2013; 17: 666
48c Kallemeyn JM. Ku Y.-Y. Mulhern MM. Bishop R. Pal A. Jacob L. Org. Process Res. Dev. 2014; 18: 191

49a Schotes C. Mezzetti A. Angew. Chem. Int. Ed. 2011; 50: 3072
49b Schotes C. Bigler R. Mezzetti A. Synthesis 2012; 44: 513
49c Enomoto K. Oyama HM. Nakada M. Chem. Eur. J. 2015; 21: 2798

50a Ito H. Hasegawa M. Takenaka Y. Kobayashi T. Iguchi K. J. Am. Chem. Soc. 2004; 126: 4520
50b Takenaka Y. Ito H. Hasegawa M. Iguchi K. Tetrahedron 2006; 62: 3380
50c Takenaka Y. Ito H. Iguchi K. Tetrahedron 2007; 63: 510

51a Shibata T. Takami K. Kawachi A. Org. Lett. 2006; 8: 1343
51b Fan B.-M. Li X.-J. Peng F.-Z. Zhang H.-B. Chan AS. C. Shao Z.-H. Org. Lett. 2010; 12: 304
51c Kossler D. Cramer N. Chem. Sci. 2017; 8: 1862

52 Grande-Carmona F. Iglesias-Sigüenza J. Álvarez E. Díez E. Fernández R. Lassaletta JM. Organometallics 2015; 34: 5073
53 García-Morales C. Ranieri B. Escofet I. López-Suarez L. Obradors C. Konovalov AI. Echavarren AM. J. Am. Chem. Soc. 2017; 139: 13628