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Tetrahedron

Volumn 52, Issue 35, 1996, Pages 11421-11444

Some novel electron transfer mediated cascade ring-opening reactions of bicyclo[4.1.0]ketones

(3) Batey, Robert A a,c Harling, John D a Motherwell, William B b

a IMPERIAL COLLEGE LONDON (United Kingdom)

b UNIVERSITY COLLEGE LONDON (United Kingdom)

c UNIVERSITY OF TORONTO (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE; CYCLOPROPANE DERIVATIVE; POLYCYCLIC HYDROCARBON; SPIRO COMPOUND;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030603096 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4020(96)00635-7 Document Type: Article

Times cited : (35)

References (71)

1
- 0003573892
- For leading references see: (a) Academic Press
- 1. For leading references see: (a) W.B. Motherwell, D. Crich, Free Radical Chain Reactions in Organic Synthesis; Academic Press, 1991.
- (1991) Free Radical Chain Reactions in Organic Synthesis
- Motherwell, W.B.¹ Crich, D.²

2
- 0003587524
- Pergamon Press, Oxford
- (b) B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, Oxford, 1986.
- (1986) Radicals in Organic Synthesis: Formation of Carbon-carbon Bonds
- Giese, B.¹

3
- 85082777144
- (c) D.P. Curran, Synthesis, 1988, 417 and 489.
- (1988) Synthesis , pp. 417
- Curran, D.P.¹

4
- 0003695099
- Georg Thieme Verlag, Stuttgart
- (d) M. Regitz, B. Giese, C-Radikale, in Houben-Weyl, Methoden der Organischen; vol. E19a, Georg Thieme Verlag, Stuttgart, 1989.
- (1989) Houben-weyl, Methoden der Organischen , vol.E19A
- Regitz, M.¹ Giese, B.² C-Radikale³

5
- 33748366516
- (e) A.L.J. Beckwith, Tetrahedron, 1981, 37, 3073.
- (1981) Tetrahedron , vol.37 , pp. 3073
- Beckwith, A.L.J.¹

6
- 0004032955
- John Wiley and Sons, New York
- (f) Free Radicals, vvol. 1 + 2, Ed. J.K. Kochi, John Wiley and Sons, New York, 1973.
- (1973) Free Radicals , vol.1-2
- Kochi, J.K.¹

7
- 0000056417
- Ed. P. deMayo, Academic Press, New York
- (g) A.L.J. Beckwith, K.U. Ingold, in Rearrangements in Ground and Excited States, Ed. P. deMayo, Academic Press, New York, 1980, 1, 162.
- (1980) Rearrangements in Ground and Excited States , vol.1 , pp. 162
- Beckwith, A.L.J.¹ Ingold, K.U.²

8
- 85034941875
- (h) D.P. Curran, Synlett, 1991, 63.
- (1991) Synlett , pp. 63
- Curran, D.P.¹

9
- 0000702878
- 2. C.P. Jasperse, D.P. Curran, T.L. Fevig, Chem. Rev., 1991, 91, 1237.
- (1991) Chem. Rev. , vol.91 , pp. 1237
- Jasperse, C.P.¹ Curran, D.P.² Fevig, T.L.³

10
- 0022405113
- 3. D.P. Curran, D.M. Rakiewicz, Tetrahedron, 1985, 41, 3943.
- (1985) Tetrahedron , vol.41 , pp. 3943
- Curran, D.P.¹ Rakiewicz, D.M.²

11
- 0000866416
- 4. (a) M. Newcomb, A.G. Glenn, W.G. Williams, J. Org. Chem., 1989, 54, 2675.
- (1989) J. Org. Chem. , vol.54 , pp. 2675
- Newcomb, M.¹ Glenn, A.G.² Williams, W.G.³

12
- 0000721223
- and references cited therein
- (b) A.L.J. Beckwith, V.W. Bowry, J. Org. Chem., 1989, 54, 2681 and references cited therein.
- (1989) J. Org. Chem. , vol.54 , pp. 2681
- Beckwith, A.L.J.¹ Bowry, V.W.²

13
- 0026782705
- 5. (a) R.A. Batey, J.D. Harling, W.B. Motherwell, Tetrahedron, 1992, 48, 8031.
- (1992) Tetrahedron , vol.48 , pp. 8031
- Batey, R.A.¹ Harling, J.D.² Motherwell, W.B.³

14
- 37049084132
- (b) J.D. Harling, W.B. Motherwell, J. Chem. Soc., Chem. Commun., 1988, 1380.
- (1988) J. Chem. Soc., Chem. Commun. , pp. 1380
- Harling, J.D.¹ Motherwell, W.B.²

15
- 37049081509
- For leading references see
- 6. For leading references see: (a) R.A. Batey, P. Grice, J.D. Harling, W.B. Motherwell, H.S. Rzepal, J. Chem. Soc., Chem. Commun., 1992, 942.
- (1992) J. Chem. Soc., Chem. Commun. , pp. 942
- Batey, R.A.¹ Grice, P.² Harling, J.D.³ Motherwell, W.B.⁴ Rzepal, H.S.⁵

16
- 0001608244
- (b) D.L.J. Clive, S. Daigneault, J. Org. Chem., 1991, 56, 3801.
- (1991) J. Org. Chem. , vol.56 , pp. 3801
- Clive, D.L.J.¹ Daigneault, S.²

17
- 37049079119
- (c) D.L.J. Clive, S. Daigneault, J. Chem. Soc., Chem. Commun., 1989, 332.
- (1989) J. Chem. Soc., Chem. Commun. , pp. 332
- Clive, D.L.J.¹ Daigneault, S.²

18
- 0000022107
- (d) D.L.J. Clive, S. Daigneault, J. Org. Chem., 1991, 56, 5285.
- (1991) J. Org. Chem. , vol.56 , pp. 5285
- Clive, D.L.J.¹ Daigneault, S.²

19
- 0000648160
- (e) B. Arreguy San Miguel, B. Maillard, B. Delmond, Tetrahedron Lett., 1987, 28, 2127.
- (1987) Tetrahedron Lett. , vol.28 , pp. 2127
- Arreguy San Miguel, B.¹ Maillard, B.² Delmond, B.³

20
- 84971043155
- (f) A.L.J. Beckwith, G. Phillipou, Aust. J. Chem., 1976, 29, 123.
- (1976) Aust. J. Chem. , vol.29 , pp. 123
- Beckwith, A.L.J.¹ Phillipou, G.²

21
- 0001434506
- (g) E.C. Friedrich, R.L. Holmstead, J. Org. Chem., 1971, 36, 971; 1972, 37, 2546; 1972, 37, 2550.
- (1971) J. Org. Chem. , vol.36 , pp. 971
- Friedrich, E.C.¹ Holmstead, R.L.²

22
- 0006940816
- (g) E.C. Friedrich, R.L. Holmstead, J. Org. Chem., 1971, 36, 971; 1972, 37, 2546; 1972, 37, 2550.
- (1972) J. Org. Chem. , vol.37 , pp. 2546

23
- 0001733006
- (g) E.C. Friedrich, R.L. Holmstead, J. Org. Chem., 1971, 36, 971; 1972, 37, 2546; 1972, 37, 2550.
- (1972) J. Org. Chem. , vol.37 , pp. 2550

24
- 0000916338
- (h) S.J. Cristol, R.V. Barbour, J. Am. Chem. Soc., 1968, 90, 2832.
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 2832
- Cristol, S.J.¹ Barbour, R.V.²

25
- 37049103968
- and references cited therein
- (i) C. Roberts, J.C. Walton, J. Chem. Soc., Perkin Trans. 2, 1983, 879 and references cited therein.
- (1983) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 879
- Roberts, C.¹ Walton, J.C.²

26
- 33947338489
- For leading references see
- 7. For leading references see: (a) W.G. Dauben, E.J. Deviny, J. Org. Chem., 1966, 31, 3794.
- (1966) J. Org. Chem. , vol.31 , pp. 3794
- Dauben, W.G.¹ Deviny, E.J.²

27
- 0000448167
- (b) T. Norin, Acta Chem. Scand., 1965, 19, 1289.
- (1965) Acta Chem. Scand. , vol.19 , pp. 1289
- Norin, T.¹

28
- 0011883142
- (c) E. Piers, P.M. Worster, J. Am. Chem. Soc., 1972, 94, 2896.
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 2896
- Piers, E.¹ Worster, P.M.²

29
- 0025086383
- (d) R.M. Cory, M.D. Bailey, D.W.C. Tse, Tetrahedron Lett., 1990, 31, 6839.
- (1990) Tetrahedron Lett. , vol.31 , pp. 6839
- Cory, R.M.¹ Bailey, M.D.² Tse, D.W.C.³

30
- 84981911085
- (e) R. Gompper, M.-L. Schwarzensteiner, Angew. Chem. (Intl. Edn. Engl.), 1982, 21, 438.
- (1982) Angew. Chem. (Intl. Edn. Engl.) , vol.21 , pp. 438
- Gompper, R.¹ Schwarzensteiner, M.-L.²

31
- 0011897422
- (f) S.K. Attah-Poku, K. Antczak, S.J. Alward, A.G. Fallis, Can. J. Chem., 1984, 62, 1717.
- (1984) Can. J. Chem. , vol.62 , pp. 1717
- Attah-Poku, S.K.¹ Antczak, K.² Alward, S.J.³ Fallis, A.G.⁴

32
- 0011886610
- (g) W.S. Murphy, S. Wattanasin, Tetrahedron Lett., 1981, 22, 695.
- (1981) Tetrahedron Lett. , vol.22 , pp. 695
- Murphy, W.S.¹ Wattanasin, S.²

33
- 0026033427
- (h) J. Cossy, P. Aclinou, V. Bellosta, J. Baranne-Lafont, D. Sparfet, C. Souchard, Tetrahedron Lett., 1991, 32, 1315.
- (1991) Tetrahedron Lett. , vol.32 , pp. 1315
- Cossy, J.¹ Aclinou, P.² Bellosta, V.³ Baranne-Lafont, J.⁴ Sparfet, D.⁵ Souchard, C.⁶

34
- 85034895022
- (i) K.J. Kulicke, B. Giese, Synlett, 1990, 91.
- (1990) Synlett , pp. 91
- Kulicke, K.J.¹ Giese, B.²

35
- 0345364982
- (j) A.G. Davies, J.-Y. Godet, B. Muggleton, M. Pereyre, J.-C. Pommier, J. Chem. Soc., Perkin Trans. 2, 1976, 1719.
- (1976) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1719
- Davies, A.G.¹ Godet, J.-Y.² Muggleton, B.³ Pereyre, M.⁴ Pommier, J.-C.⁵

36
- 0026015020
- 8. R.A. Batey, W.B. Motherwell, Tetrahedron Lett., 1991, 32, 6649.
- (1991) Tetrahedron Lett. , vol.32 , pp. 6649
- Batey, R.A.¹ Motherwell, W.B.²

37
- 33947485009
- 9. E.J. Corey, M. Chaykovsky, J. Am. Chem. Soc., 1965, 87, 1353.
- (1965) J. Am. Chem. Soc. , vol.87 , pp. 1353
- Corey, E.J.¹ Chaykovsky, M.²

38
- 37049138992
- 10. W.B. Motherwell, J. Chem. Soc., Chem. Commun., 1973, 935.
- (1973) J. Chem. Soc., Chem. Commun. , pp. 935
- Motherwell, W.B.¹

39
- 33746402465
- 11. E.J. Corey, S.G. Pyne, Tetrahedron Lett., 1983, 24, 2821.
- (1983) Tetrahedron Lett. , vol.24 , pp. 2821
- Corey, E.J.¹ Pyne, S.G.²

40
- 0041807380
- 12. (a) W.P. Griffith, S.V: Ley, G.P. Whitcombe, A.D. White, J. Chem. Soc., Chem. Commun., 1987, 1625.
- (1987) J. Chem. Soc., Chem. Commun , pp. 1625
- Griffith, W.P.¹ Ley, S.V.² Whitcombe, G.P.³ White, A.D.⁴

41
- 0002455223
- (b) W.P. Griffith, S.V. Ley, Aldrichimica Acta, 1990, 23, 13.
- (1990) Aldrichimica Acta , vol.23 , pp. 13
- Griffith, W.P.¹ Ley, S.V.²

42
- 0026060688
- 13. T. Mallät, Zs. Bodnar, J. Petrö, Tetrahedron, 1991, 47, 441.
- (1991) Tetrahedron , vol.47 , pp. 441
- Mallät, T.¹ Bodnar, Zs.² Petrö, J.³

43
- 0000358709
- 14. L. Zhu, R.M. Wehmeyer, R.D. Rieke, J. Org. Chem., 1991, 56, 1445.
- (1991) J. Org. Chem. , vol.56 , pp. 1445
- Zhu, L.¹ Wehmeyer, R.M.² Rieke, R.D.³

44
- 0025002809
- 15. (a) G.A. Kraus, S. Liras, Tetrahedron Lett., 1990, 31, 5265.
- (1990) Tetrahedron Lett. , vol.31 , pp. 5265
- Kraus, G.A.¹ Liras, S.²

45
- 37049076054
- See also reference 7
- (b) E. Hasegawa, K. Ishiyama, T. Horaguchi, T. Shimizu, J. Chem. Soc., Chem. Commun., 1990, 550. See also reference 7(i).
- (1990) J. Chem. Soc., Chem. Commun. , pp. 550
- Hasegawa, E.¹ Ishiyama, K.² Horaguchi, T.³ Shimizu, T.⁴

46
- 37049087661
- 16. (a) S.J. Cole, J.N. Kirwan, B.P. Roberts, C.R. Willis, J. Chem. Soc., Perkin Trans, 1, 1991, 103.
- (1991) J. Chem. Soc., Perkin Trans , vol.1 , pp. 103
- Cole, S.J.¹ Kirwan, J.N.² Roberts, B.P.³ Willis, C.R.⁴

47
- 2442708429
- (b) R.P. Allen, B.P. Roberts, C.R. Willis, J. Chem. Soc., Chem. Commun., 1989, 1387.
- (1989) J. Chem. Soc., Chem. Commun. , pp. 1387
- Allen, R.P.¹ Roberts, B.P.² Willis, C.R.³

48
- 0000188389
- 17. (a) A.L.J. Beckwith, D.H. Roberts, J. Am. Chem. Soc., 1986, 108, 5893.
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 5893
- Beckwith, A.L.J.¹ Roberts, D.H.²

49
- 0000860816
- (b) E.J. Enholm, G. Prasad, Tetrahedron Lett., 1989, 30, 4939.
- (1989) Tetrahedron Lett. , vol.30 , pp. 4939
- Enholm, E.J.¹ Prasad, G.²

50
- 37049076054
- (c) E. Hasegawa, K. Ishiyama, T. Horaguchi, T. Shimizu, J. Chem. Soc., Chem. Commun., 1990, 550.
- (1990) J. Chem. Soc., Chem. Commun. , pp. 550
- Hasegawa, E.¹ Ishiyama, K.² Horaguchi, T.³ Shimizu, T.⁴

51
- 0000467378
- For an example of the use of O-stannyl enolates
- 18. For an example of the use of O-stannyl enolates, see: E.J. Enholm, K.S. Kinter, J. Am. Chem. Soc., 1991, 113, 7784.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 7784
- Enholm, E.J.¹ Kinter, K.S.²

52
- 37049082202
- 19. See for example: G. Pattenden, S.J. Teague, J. Chem. Soc., Perkin Trans. 1, 1988, 1077.
- (1988) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1077
- Pattenden, G.¹ Teague, S.J.²

53
- 0011893923
- 20. (a) S.K. Pradhan, S.R. Kadam, J.N. Kolhe, J. Org. Chem., 1981, 46, 2633.
- (1981) J. Org. Chem. , vol.46 , pp. 2633
- Pradhan, S.K.¹ Kadam, S.R.² Kolhe, J.N.³

54
- 33845556646
- (b) S.K. Pradhan, S.R. Kadam, J.N. Kolhe, T.V. Radhakrishnan, S.V. Sohani, V.B. Thaker, J. Org. Chem., 1981, 46, 2622.
- (1981) J. Org. Chem. , vol.46 , pp. 2622
- Pradhan, S.K.¹ Kadam, S.R.² Kolhe, J.N.³ Radhakrishnan, T.V.⁴ Sohani, S.V.⁵ Thaker, V.B.⁶

55
- 0017317385
- (c) S.K. Pradhan, T.V. Radhakrishnan, R. Subsamianian, J. Org. Chem., 1976, 41, 1943.
- (1976) J. Org. Chem. , vol.41 , pp. 1943
- Pradhan, S.K.¹ Radhakrishnan, T.V.² Subsamianian, R.³

56
- 0001367782
- For an excellent review of samarium(II) iodide chemistry
- 21. For an excellent review of samarium(II) iodide chemistry see: G.A. Molander, Organic Reactions, 1994, 46, 211.
- (1994) Organic Reactions , vol.46 , pp. 211
- Molander, G.A.¹

57
- 33845280002
- 22. T.L. Fevig, R.L. Elliot, D.P. Curran, J. Am. Chem. Soc., 1988, 110, 5064.
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 5064
- Fevig, T.L.¹ Elliot, R.L.² Curran, D.P.³

58
- 84985052504
- 23. T. Mukhopadhay, D. Seebach, Helv. Chim. Acta, 1982, 65, 385.
- (1982) Helv. Chim. Acta , vol.65 , pp. 385
- Mukhopadhay, T.¹ Seebach, D.²

59
- 33751386286
- For a discussion of additive and solvent effects on samarium(II) iodide reductions and references cited therein
- 24. For a discussion of additive and solvent effects on samarium(II) iodide reductions see: E. Hasegawa, D.P. Curran, J. Org. Chem., 1993, 58, 5008 and references cited therein.
- (1993) J. Org. Chem. , vol.58 , pp. 5008
- Hasegawa, E.¹ Curran, D.P.²

60
- 0010530025
- 25. D.P. Curran, R.L. Wolin, Synlett, 1991, 317.
- (1991) Synlett , pp. 317
- Curran, D.P.¹ Wolin, R.L.²

61
- 33845374408
- 26. G.A. Molander, G. Hahn, J. Org. Chem., 1986, 51, 2596.
- (1986) J. Org. Chem. , vol.51 , pp. 2596
- Molander, G.A.¹ Hahn, G.²

62
- 0028609251
- 27. (a) D.L. Comins, X. Zheng, J. Chem. Soc., Chem. Commun., 1994, 2681.
- (1994) J. Chem. Soc., Chem. Commun. , pp. 2681
- Comins, D.L.¹ Zheng, X.²

63
- 0001479858
- (b) E.J. Enholm, J.A. Schreier, J. Org. Chem., 1995, 60, 1110.
- (1995) J. Org. Chem. , vol.60 , pp. 1110
- Enholm, E.J.¹ Schreier, J.A.²

64
- 33751499457
- 28. G.A. Molander, J.A. McKie, J. Org. Chem., 1991, 56, 4112.
- (1991) J. Org. Chem. , vol.56 , pp. 4112
- Molander, G.A.¹ McKie, J.A.²

65
- 0000449407
- and references cited therein
- 29. A.L.J. Beckwith, J. Zimmermann, J. Org. Chem., 1991, 56, 5791 and references cited therein.
- (1991) J. Org. Chem. , vol.56 , pp. 5791
- Beckwith, A.L.J.¹ Zimmermann, J.²

66
- 33845281219
- 30. G.A. Molander, J.B. Etter, J. Am. Chem. Soc., 1987, 109, 6556.
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 6556
- Molander, G.A.¹ Etter, J.B.²

67
- 0000228274
- 31. T. Imamoto, Y, Kamiya, T. Hatajima, H. Takahashi, Tetrahedron Lett., 1989, 30, 5149.
- (1989) Tetrahedron Lett. , vol.30 , pp. 5149
- Imamoto, T.¹ Kamiya, Y.² Hatajima, T.³ Takahashi, H.⁴

68
- 0037629474
- 32. G.A. Molander, B.E. La Belle, G, Hahn, J. Org. Chem., 1986, 51, 5259.
- (1986) J. Org. Chem. , vol.51 , pp. 5259
- Molander, G.A.¹ La Belle, B.E.² Hahn, G.³

69
- 0011886611
- 33. E. Siscovic, A.S. Rao, Curr. Sci., 1968, 37, 286.
- (1968) Curr. Sci. , vol.37 , pp. 286
- Siscovic, E.¹ Rao, A.S.²

70
- 0011812673
- 34. B. Jursic, M. Ladika, B. Bosner, R. Kobetic, D.E. Sunko, Tetrahedron, 1988, 44, 2311.
- (1988) Tetrahedron , vol.44 , pp. 2311
- Jursic, B.¹ Ladika, M.² Bosner, B.³ Kobetic, R.⁴ Sunko, D.E.⁵

71
- 0023868862
- 35. A. Murai, N. Tanimoto, N. sakamoto, T. Masamune, J. Am. Chem. Soc., 1988, 110, 1985.
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 1985
- Murai, A.¹ Tanimoto, N.² Sakamoto, N.³ Masamune, T.⁴

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