Solvent-dependent regioselectivity of hydrogen chloride-mediated ring opening of alkylidenecyclopropanone acetal

Tetrahedron Letters

Volumn 47, Issue 25, 2006, Pages 4145-4148

  Fujita, Morifumi ^a   Hanagiri, Shinji ^a   Okuyama, Tadashi ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

Br nsted acid; Cyclopropane; Regioselectivity; Ring opening

Indexed keywords

2 CYCLOHEXYLIDENE 3,3 DIMETHYLCYCLOPROPANONE ACETAL; ACETAL DERIVATIVE; CARBON; HYDROCHLORIC ACID; OXYGEN; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; PROTON TRANSPORT; RING OPENING;

EID: 33646678450     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.067     Document Type: Article

References (60)

1. For reviews, see:. Binger P., and Büch H.M. Top. Curr. Chem. 135 (1987) 77-151
2. Brandi A., and Goti A. Chem. Rev. 98 (1998) 589-635
3. Yamago S., and Nakamura E. In: Overman L.E. (Ed). Organic Reactions Vol. 61 (2002), John Wiley & Sons, Hoboken Chapter 1
4. Brandi A., Cicchi S., Cordero F.M., and Goti A. Chem. Rev. 103 (2003) 1213-1269
5. For recent examples, see:. Nakamura I., Saito S., and Yamamoto Y. J. Am. Chem. Soc. 122 (2000) 2661-2662
6. Nakamura I., Oh B.H., Saito S., and Yamamoto Y. Angew. Chem. Int. Ed. 40 (2001) 1298-1300
7. Camacho D.H., Nakamura I., Saito S., and Yamamoto Y. J. Org. Chem. 66 (2001) 270-275
8. Tantillo D., Carpenter B.K., and Hoffmann R. Organometallics 20 (2001) 4562-4564
9. Nishihara Y., Yoda C., and Osakada K. Organometallics 20 (2001) 2124-2126
10. Nüske H., Bräse S., Kozhushkov S.I., Noltemeyer M., Es-Sayed M., and de Maijere A. Chem. Eur. J. 8 (2002) 2350-2369
11. Kim S., Takeuchi D., and Osakada K. J. Am. Chem. Soc. 124 (2002) 762-763
12. Nakamura I., Siriwardana A.I., Saito S., and Yamamoto Y. J. Org. Chem. 67 (2002) 3445-3449
13. Kawasaki T., Saito S., and Yamamoto Y. J. Org. Chem. 67 (2002) 4911-4915
14. Itazaki M., Nishihara Y., and Osakada K. J. Org. Chem. 67 (2002) 6889-6895
15. Huang X., and Zhou H. Org. Lett. 4 (2002) 4419-4422
16. Siriwardana A.I., Nakamura I., and Yamamoto Y. Tetrahedon Lett. 44 (2003) 4547-4550
17. Scott M.E., Han W., and Lautens M. Org. Lett. 6 (2004) 3309-3312
18. Huang X., Zhou H., and Chen W. J. Org. Chem. 69 (2004) 839-842
19. Siriwardana A.I., Nakamura I., and Yamamoto Y. J. Org. Chem. 69 (2004) 3202-3204
20. Zhou H., Huang X., and Chen W. J. Org. Chem. 69 (2004) 5471-5472
21. López F., Delgado A., Rodríguez J.R., Castedo L., and Mascareñas J.L. J. Am. Chem. Soc. 126 (2004) 10262-10263
22. Saito S., Masuda M., and Komagawa S. J. Am. Chem. Soc. 126 (2004) 10540-10541
23. Suginome M., Matsuda T., and Ito Y. J. Am. Chem. Soc. 122 (2000) 11015-11016
24. Bapuji S.A., Motherwell W.B., and Shipman M. Tetrahedron Lett. 30 (1989) 7107-7110
25. Binger P., and Schäfer B. Tetrahedron Lett. 29 (1988) 4539-4542
26. Binger P., and Wedemann P. Tetrahedron Lett. 26 (1985) 1045-1048
27. Noyori R., Kumagai Y., Umeda I., and Takaya H. J. Am. Chem. Soc. 94 (1972) 4018-4020
28. Ma S., and Zhang J. Angew. Chem. Int. Ed. 42 (2003) 184-187
29. Ma S., Lu L., and Zhang J. J. Am. Chem. Soc. 126 (2004) 9645-9660
30. Xu G.-C., Liu L.-P., Lu J.-M., and Shi M. J. Am. Chem. Soc. 127 (2005) 14552-14553
31. Chen Y., and Shi M. J. Org. Chem. 69 (2004) 426-431
32. Shi M., Xu B., and Huang J.-W. Org. Lett. 6 (2004) 1175-1178
33. Xu B., and Shi M. Org. Lett. 5 (2003) 1415-1418
34. Shi M., Shao L.-X., and Xu B. Org. Lett. 5 (2003) 579-582
35. Shi M., and Xu B. Tetrahedron Lett. 44 (2003) 3839-3842
36. Huang J.-W., and Shi M. Tetrahedron Lett. 44 (2003) 9343-9347
37. Shi M., Chen Y., Xu B., and Tang J. Tetrahedron Lett. 43 (2002) 8019-8024
38. Shi M., and Xu B. Org. Lett. 4 (2002) 2145-2148
39. Patient L., Berry M.B., and Kilburn J.D. Tetrahedron Lett. 44 (2003) 1015-1017
40. Nakamura I., Kamada M., and Yamamoto Y. Tetrahedron Lett. 45 (2004) 2903-2906
41. Newman M.S., and Fraunfelder G. J. Org. Chem. 39 (1974) 251-252
42. Newman M.S., and Zwan M.C.V. J. Org. Chem. 39 (1974) 1186-1189
43. For recent examples, see:. Siriwardana A.I., Nakamura I., and Yamamoto Y. Tetrahedron Lett. 44 (2003) 985-987
44. Huang J.-W., and Shi M. Tetrahedron 60 (2004) 2057-2062
45. Huang J.-W., and Shi M. Synlett (2004) 2343-2346
46. Xu G.-C., Ma M., Liu L.-P., and Shi M. Synlett (2005) 1869-1872
47. Wang B.-Y., Jiang R.-S., Li J., and Shi M. Eur. J. Org. Chem. (2005) 4002-4008
48. Ikeda H., Nomura T., Akiyama K., Oshima M., Roth H.D., Tero-Kubota S., and Miyashi T. J. Am. Chem. Soc. 127 (2005) 14497-14504
49. Fujita M., Fujiwara K., Mouri H., Kazekami Y., and Okuyama T. Tetrahedron Lett. 45 (2004) 8023-8026
50. Fujita M., Fujiwara K., and Okuyama T. Chem. Lett. 35 (2006) 382-383
51. The reaction of 1b in acetonitrile preferentially gave some 4 but not 3 in addition to 2. This could be due to the C2-C3 bond cleavage via the carbon protonation. The ratio of 3/4 slightly changed depending on the conditions of the reaction of 1a, although the amount of 3 is always larger than that of 4.
52. 11b
53. Wenkert E., Mueller R.A., Reardon Jr. E.J., Sathe S.S., Scharf D.J., and Tosi G. J. Am. Chem. Soc. 92 (1970) 7428-7436
54. 12b
55. Salaun J. Chem. Rev. 83 (1983) 619-632
56. 13c
57. Stewart R. The Proton: Applications to Organic Chemistry (1985), Academic Press, Orlando pp. 251-305
58. Okuyama T. Acc. Chem. Res. 19 (1986) 370-376
59. Schowen R.L. In: Streitwieser Jr. A., and Taft R.W. (Eds). Progress in Physical Organic Chemistry Vol. 9 (1972), John Wiley & Sons, New York 275-332
60. 9a