Sequential and highly stereoselective intermolecular radical additions of 2,3-cis-disubstituted 1,1-dibromo- and 1-bromocyclopropanes to electron-deficient olefins

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1837-1840

  Tanabe, Yoo ^a   Wakimura, Ken Ichi ^a   Nishii, Yoshinori ^a  

^a KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; ORGANOBROMINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029923132     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00156-6     Document Type: Article

References (34)

1. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon, Oxford, 1986.
2. (b) Neumann, W. P. Synthesis 1987, 665.
3. (c) Curran, D. P. Synthesis 1988, 417 and 489.
4. (d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
5. Ref. 1a, Chap. 3. Ref. 1c, Chap. 2-2. Ref. 1d, p. 1252.
6. (a) Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 28, 969.
7. (b) Dolbier, W. R.; Bartberger, M. D. J. Org. Chem. 1995, 60, 4984.
8. (a) Seyferth, D.; Yamazaki, H.; Alleston, D. L. J. Org. Chem. 1963, 28, 703.
9. (b) Ando, T.; Yamanaka, H.; Namigata, F.; Funasaka, W. J. Am. Chem. Soc. 1967, 89, 5719.
10. (c) Kuivila, H. G. Synthesis 1970, 499.
11. (d) Neumann, W. P. ibid. 1987, 665.
12. (e) Nozaki, H.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547.
13. (f) Miura, K.; Ichinose, Y.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143.
14. (g) Apeloig, Y.; Nakash, M. J. Am. Chem. Soc. 1994, 116, 10084.
15. (a) Kostikov, R. R.; Mochanov, A. P.; Hopf, H. In Small Ring Compounds in Organic Synthesis IV; Meijere, A., Ed.; Topics in Current Chemistry 155; Springer-Verlag: Berlin, 1990; pp 41-46.
16. (b) Seyferth, D.; Porokai, B. J. Org. Chem. 1966, 31, 1702.
17. (c) Blankenship, R. M.; Burdett, K. A.; Swenton, J. S. ibid. 1974, 39, 2300.
18. (d) Sydnes, L. K.; SkattebØl, L. Tetrahedron Lett. 1974, 3703.
19. (e) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. J. Org. Chem. 1981, 46, 3745.
20. (f) Osuka, A.; Takechi, K.; Suzuki, H. Bull. Chem. Soc. Jpn. 1984, 57, 303.
21. (a) Kitatani, K.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1977, 50, 1600.
22. (b) Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. J. Org. Chem. 1993, 58, 2958.
23. (a) Dowd, P.; Zhang, W. J. Am. Chem. Soc. 1992, 114, 10084.
24. (b) Tanabe, Y.; Nishii, Y.; Wakimura, K. Chem. Lett., 1994. 1757.
25. (c) Lee, E.; Park, C. H.; Yun J. S. J. Am. Chem. Soc. 1995, 117, 8017.
26. (a) Seko, S.; Tanabe, Y.; Suzukamo, G. Tetrahedron Lett. 1990, 31, 6883.
27. (b) Ref. 7b.
28. (c) Nishii, Y.; Tanabe, Y. Tetrahedron Lett. 1995, 36, 8803.
29. (d) Nishii, Y.; Matsumura, H.; Muroya, Y.; Tsuchiya, T.; Tanabe, Y. Biosci. Biotech. Biochem. 1995, 59, 1355.
30. (e) Tanabe, Y.; Wakimura, K.; Nishii, Y.; Muroya, Y. Synthesis 1996, 257.
31. (f) Nishii, Y.; Wakimura, K.; Tsuchiya, T.; Nakamura, S.; Tanabe, Y. J. Chem. Soc. Perkin Trans. 1 in press.
32. -1. The relative configuration was determined by a NOESY experiment of 2b, which was derived from 2a and was prepared directly from 1a by the present first-step reaction. matrix presented
33. -1. These relative configurations were determined by NOESY experiments. matrix presented
34. DIBAL reduction of 2a gave the corresponding aldehyde, which was coupled with vinylmagnesium bromide to afford bromocyclopropane 10 in 44% overall yield.