Efficient and stereoselective rearrangement of Baylis-Hillman acetates catalyzed by gold(I) chloride/silver(I) trifluoromethanesulfonate

Synthesis

Volumn , Issue 7, 2009, Pages 1170-1174

  Liu, Yunkui ^a   Mao, Dajie ^a   Qian, Jianqiang ^a   Lou, Shaojie ^a   Xu, Zhenyuan ^a   Zhang, Yongmin ^b  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

Alk 2 enoates; Baylis Hillman acetate; Gold silver catalysis; Rearrangements; Stereoselectivity

Indexed keywords

ALK-2-ENOATES; BAYLIS-HILLMAN ACETATE; BAYLIS-HILLMAN ACETATES; GOLD/SILVER CATALYSIS; GOOD YIELD; HIGH YIELD; MILD REACTION CONDITIONS; REARRANGEMENTS; STEREOSELECTIVE REARRANGEMENT;

CATALYSIS; CHLORINE COMPOUNDS; GOLD COMPOUNDS;

STEREOSELECTIVITY;

2 (ACETOXYMETHYL)ALK 2 ENOATE; 2 ALKYLIDENECYCLOHEX 3 ENONE; ACETIC ACID; ACETIC ACID DERIVATIVE; GOLD CHLORIDE TRIFLUOROMETHANESULFONATE; GOLD SILVER TRIFLUOROMETHANESULFONATE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CHEMICAL BOND; ISOMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 67650047830     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1087971     Document Type: Article

References (86)

1. For representative reviews, see: (a) Hashmi, A. S. K. Gold Bull. 2003, 36, 3.
2. (b) Hashmi, A. S. K. Gold Bull. 2004, 37, 51.
3. (c) Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem. Int. Ed. 2006, 45, 7896.
4. (d) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
5. (e) Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
6. (f) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239.
7. (g) Arcadi, A. Chem. Rev. 2008, 108, 3266.
8. (h) Skouta, R.; Li, C.-J. Tetrahedron 2008, 64, 4917.
9. (i) Muzart, J. Tetrahedron 2008, 64, 5815.
10. For recent examples, see: (a) Lalonde, R. L.; Sherry, B. D.; Kang, E. J.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2452.
11. (b) Huang, X.; Zhang, L. J. Am. Chem. Soc. 2007, 129, 6398.
12. (c) Lavallo, V.; Frey, G. D.; Donnadieu, B.; Soleilhavoup, M.; Bertrand, G. Angew. Chem. Int. Ed. 2008, 47, 5224.
13. (d) Li, G.; Huang, X.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 6944.
14. (e) Zhang, G.; Huang, X.; Li, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 1814.
15. (f) Gorin, D. J.; Waston, I. D. G.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 3736.
16. (g) Shapiro, N.; Toste, F. D. J. Am. Chem. Soc. 2008, 130, 9244.
17. (h) Bae, H. J.; Baskar, B.; An, S. E.; Cheong, J. Y.; Thangadurai, D. T.; Hwang, I.-C.; Rhee, Y. H. Angew. Chem. Int. Ed. 2008, 47, 2263.
18. For a review, see: Marison, N.; Nolan, S. P. Angew. Chem. Int. Ed. 2007, 46, 2750.
19. For recent examples concerning gold-catalyzed skeletal rearrangement of propargylic esters, see: (a) Zhang, L.; Wang, S. J. Am. Chem. Soc. 2006, 128, 1442.
20. (b) Buzas, A.; Gagosz, F. Org. Lett. 2006, 8, 515.
21. (c) Buzas, A.; Istrate, F.; Gagosz, F. Org. Lett. 2006, 8, 1957.
22. (d) Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 8414.
23. (e) Wang, S.; Zhang, L. Org. Lett. 2006, 8, 4585.
24. (f) Buzas, A.; Gagosz, F. J. Am. Chem. Soc. 2006, 128, 12614.
25. (g) Lemière, G.; Gandon, V.; Carioys, K.; Fukuyama, T.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2007, 9, 2207.
26. (h) Yu, M.; Li, G.; Wang, S.; Zhang, L. Adv. Synth. Catal. 2007, 349, 871.
27. (i) Dudnik, A. S.; Schwier, T.; Gevorgyan, V. Org. Lett. 2008, 10, 1465.
28. (j) Li, G.; Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 3740.
29. (k) Correa, A.; Marion, N.; Fensterbank, L.; Malacria, M.; Nolan, S. P.; Cavallo, L. Angew. Chem. Int. Ed. 2008, 47, 718.
30. For rearrangements of allylic esters involving gold catalysts, see: (a) Marion, N.; Gealageas, R.; Nolan, S. P. Org. Lett. 2007, 9, 2653.
31. (b) Buzas, A. K.; Istrate, F. M.; Gagosz, F. Org. Lett. 2007, 9, 985.
32. For rearrangements of allylic esters involving other transition-metal catalysts, see: (a) Henry, P. M. J. Chem. Soc. D 1971, 328.
33. (b) Henry, P. M. J. Am. Chem. Soc. 1972, 94, 5200.
34. (c) Overman, L. E.; Campbell, C. B.; Knoll, F. M. J. Am. Chem. Soc. 1978, 100, 4822.
35. (d) Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 4, 321.
36. (e) Mukhopadhyay, M.; Reddy, M. M.; Maikap, G. C.; Iabal, J. J. Org. Chem. 1995, 60, 2670.
37. (f) Shull, B. K.; Sakai, T.; Koreeda, M. J. Am. Chem. Soc. 1996, 118, 11690.
38. (g) Krishna, P. R.; Kannan, V.; Sharma, G. V. M. Synth. Commun. 2004, 34, 55.
39. (h) Shekhar, S.; Trantow, B.; Leitner, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 11770.
40. (a) Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q.
41. (b) Ciganek, E. Org. React. 1997, 51, 201.
42. (c) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
43. (d) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
44. For recent examples, see: (a) Ranu, B. C.; Chattopadhyay, K.; Jana, R. Tetrahedron Lett. 2007, 48, 3847.
45. (b) Shatiq, Z.; Liu, L.; Liu, Z.; Wang, D.; Chen, Y.-J. Org. Lett. 2007, 9, 2525.
46. (c) Basavaiah, D.; Aravindu, K. Org. Lett. 2007, 9, 2453.
47. (d) Srihari, P.; Singh, A. P.; Basak, A.-K.; Yadav, J. S. Tetrahedron Lett. 2007, 48, 5999.
48. (e) Das, B.; Chowdhury, N.; Damondar, K.; Banerjee, J. Chem. Pharm. Bull. 2007, 55, 1274.
49. (f) Cha, M. J.; Song, Y. S.; Han, E.-G.; Lee, K.-J. J. Heterocycl. Chem. 2008, 45, 235.
50. (g) Kim, S. H.; Kim, K. H.; Kim, H. S.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1948.
51. (h) Basavaiah, D.; Reddy, R. J. Org. Biomol. Chem. 2008, 6, 1034.
52. (i) Kim, H. S.; Gowrisankar, S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 3858.
53. (j) Jiang, Y.-Q.; Shi, Y.-L.; Shi, M. J. Am. Chem. Soc. 2008, 130, 7202.
54. (a) Basavaiah, D.; Padmaja, K.; Satyanarayana, T. Synthesis 2000, 1662.
55. (b) Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2004, 25, 413.
56. (c) Basavaiah, D.; Sharada, D. S.; Veerendhar, A. Tetrahedron Lett. 2004, 45, 3081.
57. Cinnamyl alcohols are important building blocks in organic synthesis. See: (a) Shanmugam, P.; Rajasigh, P. Chem. Lett. 2002, 1212.
58. (b) Raubo, P.; Giuliano, C.; Hill, A. W.; Huscroft, L. T.; London, C.; Reeve, A.; Seward, E. M.; Swain, C. G.; Kulagowski, J. J. Synlett 2006, 600.
59. (c) Gowrisankar, S.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 929.
60. (d) Xian, M.; Alaux, S.; Sagot, E.; Gefflant, T. J. Org. Chem. 2007, 72, 7560.
61. Garrido, N. M.; Garcia, M.; Díez, D.; Sánchez, F. S.; Urones, J. G. Org. Lett. 2008, 10, 1687.
62. Basavaiah, D.; Muthukumaran, K.; Sreenivasulu, B. Synthesis 2000, 545.
63. (a) Shanmugan, P.; Rajasingh, P. Synlett 2001, 1314.
64. (b) Shanmugan, P.; Rajasingh, P. Tetrahedron 2004, 60, 9283.
65. Mason, P. H.; Emslie, W. D. Tetrahedron 1994, 50, 12001.
66. Foucaud, A.; El Guemmout, F. Bull. Soc. Chim. Fr. 1989, 403.
67. Park, J. B.; Ko, S. H.; Kim, B. G.; Hong, W. P.; Lee, K.-J. Bull. Korean Chem. Soc. 2004, 25, 27.
68. (a) Liu, Y. K.; Li, J.; Zheng, H.; Xu, D. Q.; Xu, Z. Y.; Zhang, Y. M. Synlett 2005, 2999.
69. (b) Liu, Y. K.; Xu, X. S.; Zheng, H.; Xu, D. Q.; Xu, Z. Y.; Zhang, Y. M. Synlett 2006, 571.
70. (c) Liu, Y. K.; Zheng, H.; Xu, D. Q.; Xu, Z. Y.; Zhang, Y. M. Synlett 2006, 2492.
71. (d) Liu, Y. K.; Xu, D. Q.; Xu, Z. Y.; Zhang, Y. M. Zhejiang Univ. SCIENCE B 2006, 7, 393.
72. (e) Liu, Y. K.; Xu, D. Q.; Xu, Z. Y.; Zhang, Y. M. Synlett 2007, 1671.
73. (f) Liu, Y. K.; Zheng, H.; Xu, D. Q.; Xu, Z. Y.; Zhang, Y. M. Org. Prep. Proced. Int. 2007, 39, 190.
74. (g) Liu, Y. K.; Mao, D. J.; Xu, D. Q.; Xu, Z. Y.; Zhang, Y. M. Synth. Commun. 2007, 37, 4389.
75. (h) Liu, Y. K.; Xu, D. Q.; Xu, Z. Y.; Zhang, Y. M. Heteroat. Chem. 2008, 19, 188.
76. Dar, A.; Moss, K.; Cottrill, S. M.; Parish, R. V.; McAuliffe, C. A.; Pritchard, R. G.; Beagley, B.; Sandbank, J. J. Chem. Soc., Dalton Trans. 1992, 1907.
77. For an excellent review on ligand effects in homogeneous gold catalysis, see: Grorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351.
78. For silver salt additives in gold catalysis, see, for example: (a) Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem. Int. Ed. 2004, 43, 2402.
79. (b) Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2007, 9, 4821.
80. (c) Lemière, G. G.; Gandon, V.; Agenet, N.; Goddard, J.-P.; de Kozak, A. D.; Aubert, C.; Fensterbank, L.; Malacria, M. C. Angew. Chem. Int. Ed. 2006, 45, 7596.
81. (d) Shi, Z.; He, C. J. Am. Chem. Soc. 2004, 126, 5964.
82. Shafiq, Z.; Liu, L.; Liu, Z.; Wang, D.; Chen, Y. J. Org. Lett. 2007, 9, 2025.
83. A referee commented that the loss of 1,3-diaxial repulsion between the methoxycarbonyl or R group and the acetal oxygens may be another factor why intermediate 7 is not destabilized so much (see Scheme 5).
84. (a) Hoffman, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1983, 22, 795.
85. (b) Lee, K. Y.; GowriSankar, S.; Kim, J. N. Tetrahedron Lett. 2004, 45, 5485.
86. (c) David, H. O.; Kenneth, M. N. J. Org. Chem. 2003, 68, 6427.