Rhodium-catalyzed carbonylation of cyclopropyl substituted propargyl esters: A tandem 1,3-acyloxy migration [5 + 1] cycloaddition

Journal of Organic Chemistry

Volumn 77, Issue 15, 2012, Pages 6463-6472

  Shu, Dongxu ^a   Li, Xiaoxun ^a   Zhang, Min ^a   Robichaux, Patrick J ^a   Guzei, Ilia A ^a   Tang, Weiping ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLOXY GROUPS; ALLENES; CYCLOHEXENONES; CYCLOPROPYL; FUNCTIONALIZATIONS; FUNCTIONALIZED; PROPARGYL; RHODIUM-CATALYZED; TANDEM REACTION;

CARBONYLATION; CATALYSIS; ESTERIFICATION; ESTERS; HYDROCARBONS; KETONES;

RHODIUM;

1 (2 METHYL 6 OXOCYCLOHEX 2 EN 1 YLIDENE) 3 [(TRIISOPROPYLSILYL)OXY]PROPYL PIVALATE; 1 (2 METHYL 6 OXOCYCLOHEX 2 EN 1 YLIDENE) 4 PHENYLBUTYL ACETATE; 1 (2 METHYL 6 OXOCYCLOHEX 2 EN 1 YLIDENE) 4 PHENYLBUTYL PIVALATE; 1 (2 METHYL 6 OXOCYCLOHEX 2 EN 1 YLIDENE)PROPANE 1,3 DIYL BIS(2,2 DIMETHYLPROPANOATE); 1 (2,3 DIMETHYL 6 OXOCYCLOHEX 2 EN 1 YLIDENE)BUTYL PIVALATE; 1 [4 METHYL 4 (4 METHYLPENT 3 EN 1 YL) 6 OXOCYCLOHEX 2 EN 1 YLIDENE] 4 PHENYLBUTYL PIVALATE; 1 [6 OXO 3 [(TRIISOPROPYLSILYL)OXY]CYCLOHEX 2 EN 1 YLIDENE] 4 PHENYLBUTYL PIVALATE; 2,2 DIMETHYL 1 (6 OXOCYCLOHEX 2 EN 1 YLIDENE)PROPYL PIVALATE; 2,2 DIMETHYLPROPIONIC ACID 3 ACETOXYMETHYL 6 ISOPROPYLIDENE 5 OXO CYCLOHEX 1 ENYL ESTER; 2,2 DIMETHYLPROPIONIC ACID 6 ISOPROPYLIDENE 3 METHOXYMETHYL 5 OXO CYCLOHEX 1 ENYL ESTER; CYCLOHEXANONE; CYCLOPROPANE; CYCLOPROPYL PROPARGYL ESTER; ESTER DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLOADDITION; ISOMERISM; ISOMERIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

CARBON MONOXIDE; CATALYSIS; CYCLIZATION; CYCLOPROPANES; ESTERS; KETONES; MOLECULAR STRUCTURE; RHODIUM;

EID: 84864592904     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300973r     Document Type: Article

References (90)

1. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49
2. Fruhauf, H. W. Chem. Rev. 1997, 97, 523
3. Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813
4. Evans, P. A. Modern Rhodium-Catalyzed Organic Reactions; Wiley-VCH: Weinheim, 2005.
5. Michelet, V.; Toullec, P. Y.; Genet, J. P. Angew. Chem., Int. Ed. 2008, 47, 4268
6. Yu, Z.; Wang, Y.; Wang, Y. Chem.-Asian J. 2010, 5, 1072
7. Inglesby, P. A.; Evans, P. A. Chem. Soc. Rev. 2010, 39, 2791
8. Danishefsky, S. Acc. Chem. Res. 1981, 14, 400
9. Winkler, J. D. Chem. Rev. 1996, 96, 167
10. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668
11. Takao, K.; Munakata, R.; Tadano, K. Chem. Rev. 2005, 105, 4779
12. For our communication of preliminary results on 1,3-acyloxy migration [5 + 1] cycloaddition with CO, see: Shu, D.; Li, X.; Zhang, M.; Robichaux, P. J.; Tang, W. Angew. Chem., Int. Ed. 2011, 50, 1346
13. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
14. Zhu, Z.-B.; Wei, Y.; Shi, M. Chem. Soc. Rev. 2011, 40, 5534
15. Xu, H.; Zhang, W.; Shu, D.; Werness, J. B.; Tang, W. Angew. Chem., Int. Ed. 2008, 47, 8933
16. Um, J. M.; Xu, H.; Houk, K. N.; Tang, W. J. Am. Chem. Soc. 2009, 131, 6664
17. Barluenga, J.; Riesgo, L.; Lopez, L. A.; Rubio, E.; Tomas, M. Angew. Chem., Int. Ed. 2009, 48, 7569
18. Li, C.-W.; Pati, K.; Lin, G.-Y.; Abu Sohel, S. M.; Hung, H.-H.; Liu, R.-S. Angew. Chem., Int. Ed. 2010, 49, 9891
19. Trost, B. M. Science 1991, 254, 1471
20. Trost, B. M. Angew. Chem., Int. Ed. 1995, 34, 259
21. Rautenstrauch, V. J. Org. Chem. 1984, 49, 950
22. Rautenstrauch, V. Tetrahedron Lett. 1984, 25, 3845
23. Mainetti, E.; Mouries, V.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. Angew. Chem., Int. Ed. 2002, 41, 2132
24. Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505
25. Miki, K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 2003, 44, 2019
26. Fürstner, A.; Hannen, P. Chem. Commun. 2004, 2546
27. Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654
28. Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mouries, V.; Dhimane, A. L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656
29. Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802
30. Prasad, B. A. B.; Yoshimoto, F. K.; Sarpong, R. J. Am. Chem. Soc. 2005, 127, 12468
31. Johansson, M. J.; Gorin, D. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 18002
32. Shibata, Y.; Noguchi, K.; Tanaka, K. J. Am. Chem. Soc. 2010, 132, 7896
33. Shibata, Y.; Noguchi, K.; Tanaka, K. Org. Lett. 2010, 12, 5596
34. Brancour, C.; Fukuyama, T.; Ohta, Y.; Ryu, I.; Dhimane, A. L.; Fensterbank, L.; Malacria, M. Chem. Commun. 2010, 46, 5470
35. Shu, X.-Z.; Huang, S.; Shu, D.; Guzei, I. A.; Tang, W. Angew. Chem., Int. Ed. 2011, 50, 8153
36. Shu, X.-Z. L., X.; Shu, D.; Huang, S.; Schienebeck, C. M.; Zhou, X.; Robichaux, P. J.; Tang, W. J. Am. Chem. Soc. 2012, 134, 5211
37. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590
38. Ma, S. Chem. Rev. 2005, 105, 2829
39. Inagaki, F.; Kitagaki, S.; Mukai, C. Synlett 2011, 594
40. Aubert, C.; Fensterbank, L.; Garcia, P.; Malacria, M.; Simonneau, A. Chem. Rev. 2011, 111, 1954
41. Brummond, K. M.; Deforrest, J. E. Synthesis 2007, 795
42. Yu, S.; Ma, S. Chem. Commun. 2011, 47, 5384
43. Von, G. Saucy; Marbet, R.; Lindlar, H.; Isler, O. Helv. Chim. Acta 1959, 42, 1945
44. Sromek, A. W.; Kel'in, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280
45. Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804
46. Zhang, L.; Wang, S. J. Am. Chem. Soc. 2006, 128, 1442
47. Zhao, J.; Hughes, C. O.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 7436
48. Buzas, A.; Gagosz, F. J. Am. Chem. Soc. 2006, 128, 12614
49. Marion, N.; Diez-Gonzalez, S.; De Fremont, P.; Noble, A. R.; Nolan, S. P. Angew. Chem., Int. Ed. 2006, 45, 3647
50. Barluenga, J.; Riesgo, L.; Vicente, R.; Lopez, L. A.; Tomas, M. J. Am. Chem. Soc. 2007, 129, 7772
51. Schwier, T.; Sromek, A. W.; Yap, D. M. L.; Chernyak, D.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 9868
52. Lemiere, G.; Gandon, V.; Cariou, K.; Fukuyama, T.; Dhimane, A. L.; Fensterbank, L.; Malacria, M. Org. Lett. 2007, 9, 2207
53. Amijs, C. H. M.; Opez-Carrillo, V.; Echavarren, A. M. Org. Lett. 2007, 9, 4021
54. Luo, T. P.; Schreiber, S. L. Angew. Chem., Int. Ed. 2007, 46, 8250
55. Wang, S.; Zhang, G.; Zhang, L. Synlett 2010, 692
56. Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750
57. Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410
58. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180
59. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2008, 47, 6754
60. Li, Z. G.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239
61. Jimenez-Nunez, E.; Echavarren, A. M. Chem. Rev. 2008, 108, 3326
62. Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351
63. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2010, 49, 5232
64. Wang, S.; Zhang, L. J. Am. Chem. Soc. 2006, 128, 8414
65. Mauleon, P.; Krinsky, J. L.; Toste, F. D. J. Am. Chem. Soc. 2009, 131, 4513
66. Garayalde, D.; Gomez-Bengoa, E.; Huang, X. G.; Goeke, A.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 4720
67. Taber, D. F.; Kanai, K.; Jiang, Q.; Bui, G. J. Am. Chem. Soc. 2000, 122, 6807
68. Kurahashi, T.; De Meijere, A. Synlett 2005, 2619
69. Iwasawa, N.; Owada, Y.; Matsuo, T. Chem. Lett. 1995, 115
70. Owada, Y.; Matsuo, T.; Iwasawa, N. Tetrahedron 1997, 53, 11069
71. Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4
72. Wender, P. A.; Deschamps, N. M.; Sun, R. Angew. Chem., Int. Ed. 2006, 45, 3957
73. Zhang, M.; Tang, W. Org. Lett. 2012, 10.1021/ol301614v
74. Jiang, G.-J.; Fu, X.-F.; Li, Q.; Yu, Z.-X. Org. Lett. 2012, 14, 692
75. Li, X.; Zhang, M.; Shu, D.; Robichaux, P. J.; Huang, S.; Tang, W. Angew. Chem., Int. Ed. 2011, 50, 10421
76. Huang, S.; Li, X.; Lin, C. L.; Guzei, I. A.; Tang, W. Chem. Commun. 2012, 48, 2204
77. Li, X.; Huang, S.; Schienebeck, C. M.; Shu, D.; Tang, W. Org. Lett. 2012, 14, 1584
78. Kobayashi, T.; Koga, Y.; Narasaka, K. J. Organomet. Chem. 2001, 624, 73
79. Wang, Y.; Wang, J.; Su, J. C.; Huang, F.; Jiao, L.; Liang, Y.; Yang, D.; Zhang, S.; Wender, P. A.; Yu, Z. J. Am. Chem. Soc. 2007, 129, 10060 and ref 18
80. For a report on regioselective isomerization of allenylcyclopropane to cyclopentene, see: Hayashi, M.; Ohmatsu, T.; Meng, Y. P.; Saigo, K. Angew. Chem., Int. Ed. 1998, 37, 837
81. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442
82. Wender, P. A.; Dyckman, A. J. Org. Lett. 1999, 1, 2089
83. Wender, P. A.; Nuss, J.; Smith, D. B.; Suarez-Sobrino, A.; Vgberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908
84. Trost, B. M.; Shen, H. C. Org. Lett. 2000, 2, 2523
85. Trost, B. M.; Shen, H. C. Angew. Chem., Int. Ed. 2001, 40, 2313
86. Trost, B. M.; Shen, H. C.; Horne, D. B.; Toste, F. D.; Steinmetz, B. G.; Koradin, C. Chem.-Eur. J. 2005, 11, 2577
87. Liu, P.; Sirois, L. E.; Cheong, P. H. Y.; Yu, Z.; Hartung, I. V.; Rieck, H.; Wender, P. A.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 10127
88. Aissa, C. Synthesis 2011, 3389
89. Zou, Y.; Garayalde, D.; Wang, Q. R.; Nevado, C.; Goeke, A. Angew. Chem., Int. Ed. 2008, 47, 10110
90. Wang, Y.-M.; Kuzniewski, C. N.; Rauniyar, V.; Hoong, C.; Toste, F. D. J. Am. Chem. Soc. 2011, 133, 12972