Stereospecific synthesis of alkylidenecyclopropanes via sequential cyclopropene carbomagnesation/1,3-carbon shift

Journal of Organic Chemistry

Volumn 75, Issue 11, 2010, Pages 3847-3850

  Xie, Xiaocong ^a   Yang, Zhe ^a   Fox, Joseph M ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLIDENECYCLOPROPANES; CYCLOPROPENE DERIVATIVES; CYCLOPROPENES; GRIGNARD REAGENT; SHIFT REACTIONS; STEREOSELECTIVE REACTIONS; STEREOSPECIFIC; STEREOSPECIFIC SYNTHESIS;

PROPYLENE;

SYNTHESIS (CHEMICAL);

ALKYLIDENECYCLOPROPANE DERIVATIVE; CARBON; CYCLOPROPANE DERIVATIVE; GRIGNARD REAGENT; UNCLASSIFIED DRUG;

ARTICLE; GRIGNARD REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

CYCLOPROPANES; STEREOISOMERISM;

EID: 77953018231     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1002938     Document Type: Article

References (79)

1. Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589
2. Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213
3. Nakamura, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 344, 111
4. Fürstner, A.; Aissa, C. J. Am. Chem. Soc. 2006, 128, 6306
5. Chowdhury, M. A.; Senboku, H.; Tokuda, M. Tetrahedron Lett. 2003, 44, 3329
6. Liang, Y.; Jiao, L.; Wang, Y.; Chen, Y.; Ma, L.; Xu, J.; Zhang, S.; Yu, Z.-X. Org. Lett. 2006, 8, 5877
7. Taillier, C.; Lautens, M. Org. Lett. 2007, 9, 591
8. Scott, M. E.; Lautens, M. Org. Lett. 2005, 7, 3045
9. Nair, V.; Suja, T. D.; Mohanan, K. Synthesis 2006, 2531
10. Siriwardana, A. I.; Nakamura, I.; Yamamoto, Y. J. Org. Chem. 2004, 69, 3202
11. Durán, J.; Gulías, M.; Castedo, L.; Mascareas, J. L. Org. Lett. 2005, 7, 5693
12. Lautens, M.; Ren, Y.; Delanghe, P. J. Am. Chem. Soc. 1994, 116, 8821
13. Lautens, M.; Ren, Y. J. Am. Chem. Soc. 1996, 118, 9597
14. Kamikawa, K.; Shimizu, Y.; Takemoto, S.; Matsuzaka, H. Org. Lett. 2006, 8, 4011
15. de Meijere, A.; Kurahashi, T. Angew. Chem., Int. Ed. 2005, 44, 7881
16. de Meijere, A.; Becker, H.; Stolle, A.; Kozhushkov, S. I.; Bes, M. T.; Salaün, J.; Noltemeyer, M. Chem.-Eur. J. 2005, 11, 2471
17. Molchanov, A. P.; Diev, V. V.; Magull, J.; Vidović, D.; Kozhushkov, S. I.; de Meijere, A.; Kostikov, R. R. Eur. J. Org. Chem. 2005, 593
18. Hu, B.; Zhu, J.; Xing, S.; Fang, J.; Du, D.; Wang, Z. Chem.-Eur. J. 2009, 15, 324
19. Zhou, H.; Huang, X.; Chen, W. Synlett. 2003, 13, 2080
20. Shi, M.; Shao, L.-X. Synlett. 2004, 5, 807
21. Zhu, Z.-b.; Liu, L.-p.; Shao, L.-x.; Shi, M. Synlett. 2007, 115
22. Shi, M.; Jiang, M.; Liu, L.-p. Org. Biomol. Chem. 2007, 5, 438
23. Shi, M.; Liu, L.-p.; Tang, J. Org. Lett. 2006, 8, 4043
24. Chen, W.-l.; Su, C.-l.; Huang, X. Synlett 2006, 9, 1446
25. Huang, X.; Fu, W.-J. Synthesis 2006, 6, 1016
26. Huang, X.; Yang, Y. Org. Lett. 2007, 9, 1667
27. Yang, Y.; Huang, X. J. Org. Chem. 2008, 73, 4702
28. Taniguchi, H.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 11298
29. Ohmura, T.; Taniguchi, H.; Kondo, Y.; Suginome, M. J. Am. Chem. Soc. 2007, 129, 3518
30. Hayashi, N.; Hirokawa, Y.; Shibata, I.; Yasuda, M.; Baba, A. J. Am. Chem. Soc. 2008, 130, 2912
31. Rahman, W.; Kuivila, H. G. J. Org. Chem. 1966, 31, 772
32. Satoh, T.; Saito, S. Tetrahedron Lett. 2004, 45, 347
33. Ma, S.; Lu, L.; Zhang, J. J. Am. Chem. Soc. 2004, 126, 9645
34. Meijs, G. F.; Eichinger, P. C. H. Tetrahedron Lett. 1987, 28, 5559
35. Stafford, J. A.; McMurry, J. E. Tetrahedron Lett. 1988, 29, 2531
36. Danheiser, R. L.; Lee, T. W.; Menichincheri, M.; Brunelli, S.; Nishiuchi, M. Synlett 1997, 469
37. Bernard, A. M.; Frongia, A.; Piras, P. P.; Secci, F. Synlett 2004, 1064
38. Bigeault, J.; Giordano, L.; de Riggi, I.; Gimbert, Y.; Buono, G. Org. Lett. 2007, 9, 3567
39. Shono, T.; Nagasawa, T.; Tsubouchi, A.; Takeda, T. Tetrahedron Lett. 2007, 48, 3521
40. Thomas, E.; Kasatkin, A. N.; Whitby, R. J. Tetrahedron Lett. 2006, 47, 9181
41. Weatherhead-Kloster, R.; Corey, E. J. Org. Lett. 2006, 8, 171
42. Rubina, M.; Woodward, E. W.; Rubin, M. Org. Lett. 2007, 9, 5501
43. Masarwa, A.; Stanger, A.; Marek, I. Angew. Chem., Int. Ed. 2007, 46, 8039
44. Simaan, S.; Masarwa, A.; Bertus, P.; Marek, I. Angew. Chem., Int. Ed. 2006, 45, 3963
45. Simaan, S.; Marek, I. Org. Lett. 2007, 9, 2569
46. Simaan, S.; Marek, I. Chem. Commun. 2009, 292
47. Feist, F. Liebigs Ann. 1924, 436, 125
48. Goss, F. R.; Ingold, C. K.; Thrope, J. F. J. Chem. Soc., Trans. 1925, 127, 460
49. Kon, G. A. R.; Nanji, H. R. J. Chem. Soc. 1932, 2557
50. Ettlinger, M. G. J. Am. Chem. Soc. 1952, 74, 5805
51. Gajewski, J. J. J. Am. Chem. Soc. 1968, 90, 7178
52. Ullman, E. F.; Fanshawe, W. J. J. Am. Chem. Soc. 1961, 83, 2379
53. Sanjiki, T.; Kato, H.; Ohta, M. Chem. Commun. 1968, 496
54. Crandall, J. K.; Paulson, D. R. J. Am. Chem. Soc. 1966, 88, 4302
55. Dolbier, W. R.; Lomas, J. D.; Tarrant, P. J. Am. Chem. Soc. 1968, 90, 3594
56. Shields, T. C.; Shoulders, B. A.; Krause, J. F.; Osborn, L. C.; Gardner, P. D. J. Am. Chem. Soc. 1965, 87, 3026
57. Creary, X. J. Org. Chem. 1978, 43, 1777
58. Creary, X. J. Org. Chem. 1980, 45, 280
59. Creary, X.; Losch, A.; Sullivan, W. J. Org. Chem. 2007, 72, 7930
60. Creary, X.; Mehrsheikh-Mohammadia, M. E. J. Org. Chem. 1986, 51, 2664
61. Nakamura, E.; Yamago, S.; Ejiri, S.; Dorigo, A. E.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 3183
62. Yang, Z.; Xie, X.; Fox, J. M. Angew. Chem., Int. Ed. 2006, 45, 3960 For related work on diastereoselective carbomagnesiation
63. Liao, L.; Fox, J. M. J. Am. Chem. Soc. 2002, 124, 14322
64. Liu, X.; Fox, J. M. J. Am. Chem. Soc. 2006, 128, 5600
65. Yan, N.; Liu, X.; Fox, J. M. J. Org. Chem. 2008, 73, 563
66. Davies, H. M. L.; Lee, G. H. Org. Lett. 2004, 6, 1233
67. Gajewski, J. J. J. Am. Chem. Soc. 1971, 93, 4450
68. Liao, L.-A.; Zhang, F.; Olga, D.; Bach, R. D.; Fox, J. M. J. Am. Chem. Soc. 2004, 126, 4490
69. Davies, H. M. L.; Bruzinski, P. R.; Fall, M. J. Tetrahedron Lett. 1996, 37, 4133
70. Ullman, E. F. J. Am. Chem. Soc. 1960, 82, 505
71. Diradical intermediate mechanistic proposals for the methylenecyclopropane rearrangement: Doering, W.; von, E.; Roth, H. D. Tetrahedron 1970, 26, 2825
72. Doering, W.; von, E.; Birladeanu, L. Tetrahedron 1973, 29, 499
73. Diradical transition state mechanistic proposal for the methylenecyclopropane rearrangement: Buchwalter, S. L. Tetrahedron 1984, 40, 5097
74. Concerted mechanistic proposals for the methylenecyclopropane rearangement: Zimmerman, H. E. Acc. Chem. Res. 1971, 4, 272
75. Dewar, M. J. S. Angew. Chem., Int. Ed. 1971, 10, 761
76. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. 1969, 8, 781
77. Heilbronner, E. Tetrahedron Lett. 1964, 5, 1923
78. Berson, J. A.; Nelson, G. L. J. Am. Chem. Soc. 1967, 89, 5503
79. Berson, J. A.; Salem, L. J. Am. Chem. Soc. 1972, 94, 8917