Asymmetric synthesis of medium-sized rings by intramolecular au(I)-catalyzed cyclopropanation

Journal of the American Chemical Society

Volumn 131, Issue 6, 2009, Pages 2056-2057

  Watson, Iain D G ^a   Ritter, Stefanie ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; GOLD; ORGANIC COMPOUNDS;

8-MEMBERED RING; ASYMMETRIC SYNTHESIS; CARBENOID; CYCLOPROPANATION; EFFICIENT METHOD; HIGH ENANTIOSELECTIVITY;

GOLD COMPOUNDS;

GOLD; TRANSITION ELEMENT; TRIPHENYLPHOSPHINE; ALKYNE; CYCLOHEPTANE DERIVATIVE; CYCLOOCTANE DERIVATIVE; CYCLOPROPANE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS LINKING; CYCLOPROPANATION; ENANTIOSELECTIVITY; SYNTHESIS; CHEMISTRY; CYCLIZATION;

ALKYNES; CATALYSIS; CYCLIZATION; CYCLOHEPTANES; CYCLOOCTANES; CYCLOPROPANES; GOLD;

EID: 67749086553     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8085005     Document Type: Article

References (50)

1. (a) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
2. (b) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881.
3. Yet, L. Chem. Rev. 2000, 100, 2963.
4. For asymmetric transition metal catalyzed synthesis of medium-sized rings by: C-C bond formation: (a) Wender, P. A.; Haustedt, L. O.; Lim, J.; Love, J. A.; Williams, T. J.; Yoon, J.-Y. J. Am. Chem. Soc. 2006, 128, 6302.
5. (b) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H J. Am. Chem. Soc. 2002, 124, 2868.
6. (c) Weatherhaed, G. A.; Cortez, G. A.; Schrock, R. R.; Hoveyda, A. H. Proc. Nat. Acad. Sci. U.S.A. 2004, 101, 5805.
7. (d) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513.
8. C-O bond formation: (e) Shen, Z.; Khan, H. A.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2916.
9. (a) Doyle, M. P.; Hu, W.; Chapman, B.; Marnett, A. B.; Peterson, C. S.; Vitale, J. P.; Stanley, S. A. J. Am. Chem. Soc. 2000, 122, 5718.
10. (b) Doyle, M. P.; Peterson, C. S.; Protopopova, M. N.; Marnett, A. B.; Parker, D. L.; Ene, D. G.; Lynch, V. J. Am. Chem. Soc. 1997, 119, 8826. For medium- sized ring formation with rhodium carbenes, see :
11. (c) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
12. (a) Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002.
13. (b) Gorin, D. J.; Dube, P.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 14480.
14. (c) Amijs, C. H. M.; Lopé-Carrillo, V.; Echavarren, A. M. Org. Lett. 2007, 9, 4021.
15. (d) Gorin, D. J.; Watson, I. D. G.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 3736.
16. (e) Davies, P. W.; Albrecht, S. J.-C. Chem. Commun. 2008, 238.
17. (f) Shapiro, N. D.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244.
18. For representative examples of intermolecular annulations: (a) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405.
19. (b) Melhado, A. D.; Luparia, M.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12638.
20. (c) Zhang, G.; Huang, X.; Li, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 1814.
21. For general reviews on Au chemistry, see: (a) Jiménez- Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326.
22. (b) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.
23. (c) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
24. (d) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.
25. (e) Furstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
26. Muñoz, M. P.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Organometallics 2005, 24, 1293.
27. (a) Boyer, F.-D.; Le Goff, X.; Hanna, I. J. Org. Chem. 2008, 73, 5163.
28. (b) Moreau, X.; Goddard, J.-P.; Bernard, M.; Lemière, G.; López-Romero, J. M.; Mainetti, E.; Marion, N.; Mouriès, V.; Thorimbert, S.; Fensterbank, L.; Malacria, M. Adv. Synth. Catal. 2008, 350, 43.
29. (c) Comer, E.; Rohan, E.; Deng, L., Jr Org. Lett. 2007, 9, 2123.
30. (d) Ferrer, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 1105.
31. (e) Bhunia, S.; Liu, R.-S. J. Am. Chem. Soc. 2008, 130, 16488.
32. For additional information see the Supporting Information.
33. This is partially due to the formation of indene byproducts : (a) Marion, N.; Díez-Gonzalez, S.; de Frémont, P.; Noble, A. R.; Nolan, S. P. Angew. Chem., Int. Ed. 2006, 45, 3647.
34. (b) Nakanishi, Y.; Miki, K.; Ohe, K. Tetrahedron 2007, 63, 12138.
35. This contrasts with secondary alkyl propargyl esters which undergo Au(I)- catalyzed cycloisomerizations to give 5- and 6-membered ring products: (a) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654.
36. (b) Furstner, A.; Hannen, P. Chem.-Eur. J. 2006, 12, 3006.
37. (c) Fehr, C.; Galindo, J. Angew. Chem., Int. Ed. 2006, 45, 2901.
38. Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5799.
39. Under identical reaction conditions, the corresponding propargyl alcohol and methyl ether gave no reaction, suggesting an enyne first mechanism is not operative. See ref 12c.
40. Soriano, E.; Marco-Contelles, J. Chem.-Eur. J. 2008, 14, 6771.
41. The absence of intermolecular products in the case of tertiary propargyl esters may reflect a decrease in the relative thermodynamic stability of the trans-intermediate of type A.
42. (a) Olefin isomerizations have been observed in rhodium-stabilized vinyl carbenoids. See: Davies, H. M. L.; Hodges, L. M.; Matasi, J. J.; Hansen, T.; Stafford, D. G. Tetrahedron Lett. 1998, 4417.
43. (b) For a discussion of isomerization of allyl cations, see: Mayr, H.; Forner, W.; von Ragué Schleyer, P. J. Am. Chem. Soc. 1979, 101, 6032.
44. (a) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249.
45. (b) Lie, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526.
46. (c) Lie, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198.
47. (d) Lie, A.; He, M.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 11472.
48. (e) Hatano, M.; Mikami, K. J. Am. Chem. Soc. 2003, 125, 4704.
49. (f) Mikami, K.; Kataika, S.; Yusa, Y.; Aikawa, K. Org. Lett. 2004, 6, 3699.
50. (g) Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2007, 127, 2764.