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Journal of Organic Chemistry

Volumn 63, Issue 24, 1998, Pages 9031-9036

Intramolecular ketone-nitrile reductive coupling reactions promoted by Samarium(II) iodide

(2) Molander, Gary A a Wolfe, Chad N a

a UNIVERSITY OF COLORADO (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IODIDE; KETOL; KETONE; NITRILE; SAMARIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0031794269 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo981537m Document Type: Article

Times cited : (74)

References (78)

1
- 33847086035
- (a) Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693,
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 2693
- Girard, P.¹ Namy, J.L.² Kagan, H.B.³

2
- 0000394141
- (b) Molander, G. A.; Kenny, C. Tetrahedron Lett. 1987, 28, 4367.
- (1987) Tetrahedron Lett. , vol.28 , pp. 4367
- Molander, G.A.¹ Kenny, C.²

3
- 0642299055
- (c) Molander, G. A.; Kenny, C. J. Org. Chem. 1988,53, 2132.
- (1988) J. Org. Chem. , vol.53 , pp. 2132
- Molander, G.A.¹ Kenny, C.²

4
- 33845280002
- (d) Fevig, T. L.; Elliot, R. L.; Curran, D. P. 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

5
- 0001764957
- (e) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8236
- Molander, G.A.¹ Kenny, C.²

6
- 0000357782
- (f) Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063.
- (1989) Tetrahedron Lett. , vol.30 , pp. 1063
- Enholm, E.J.¹ Trivellas, A.²

7
- 0000579244
- (g) Enholm, E. J.; Trivellas, A. J. Am. Chem. Soc. 1989, 111, 6463.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 6463
- Enholm, E.J.¹ Trivellas, A.²

8
- 0024788923
- (h) Enholm, E. J.; Satici, H.; Trivellas, A. J. Org. Chem. 1989, 54, 5841.
- (1989) J. Org. Chem. , vol.54 , pp. 5841
- Enholm, E.J.¹ Satici, H.² Trivellas, A.³

9
- 0025145919
- (i) Bannai, K.; Tanaka, T.; Okamura, N.; Hazato, A.; Sugiura, S.; Manabe, K; Tomimori, K.; Kato, Y.; Kurozumi, S.; Noyori, R. Tetrahedron 1990, 31, 6689.
- (1990) Tetrahedron , vol.31 , pp. 6689
- Bannai, K.¹ Tanaka, T.² Okamura, N.³ Hazato, A.⁴ Sugiura, S.⁵ Manabe, K.⁶ Tomimori, K.⁷ Kato, Y.⁸ Kurozumi, S.⁹ Noyori, R.¹⁰

10
- 0000055876
- (j) Molander, G. A.; Kenny, C. J. Org. Chem. 1991, 56, 1439.
- (1991) J. Org. Chem. , vol.56 , pp. 1439
- Molander, G.A.¹ Kenny, C.²

11
- 33751392448
- (k) Molander, G. A.; McKie, J. A. J. Org. Chem. 1992, 57, 3132.
- (1992) J. Org. Chem. , vol.57 , pp. 3132
- Molander, G.A.¹ McKie, J.A.²

12
- 0026536250
- (l) Baldwin, J. E.; Mackenzie Turner, S. C.; Moloney, M. G. Tetrahedron Lett. 1992, 33, 1517.
- (1992) Tetrahedron Lett. , vol.33 , pp. 1517
- Baldwin, J.E.¹ Mackenzie Turner, S.C.² Moloney, M.G.³

13
- 0027085902
- (m) Tadano, K.; Isshiki, Y.; Minami, M.; Ogawa, S. Tetrahedron Lett. 1992, 33, 7899.
- (1992) Tetrahedron Lett. , vol.33 , pp. 7899
- Tadano, K.¹ Isshiki, Y.² Minami, M.³ Ogawa, S.⁴

14
- 0027133030
- (n) Tadano, K.; Isshiki, Y.; Minami, M.; Ogawa, S. J. Org. Chem. 1993, 58, 6266.
- (1993) J. Org. Chem. , vol.58 , pp. 6266
- Tadano, K.¹ Isshiki, Y.² Minami, M.³ Ogawa, S.⁴

15
- 0000210522
- (o) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186.
- (1994) J. Org. Chem. , vol.59 , pp. 3186
- Molander, G.A.¹ McKie, J.A.²

16
- 0028218744
- (p) Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1994, 35, 1627.
- (1994) Tetrahedron Lett. , vol.35 , pp. 1627
- Enholm, E.J.¹ Trivellas, A.²

17
- 0028129634
- (q) Baldwin, J. E.; Mackenzie Turner, S. C.; Moloney, M. G. Tetrahedron 1994, 50, 9411.
- (1994) Tetrahedron , vol.50 , pp. 9411
- Baldwin, J.E.¹ Mackenzie Turner, S.C.² Moloney, M.G.³

18
- 0027936934
- (r) Baldwin, J. E.; Mackenzie Turner, S. C.; Moloney, M. G. Tetrahedron 1994, 50, 9425.
- (1994) Tetrahedron , vol.50 , pp. 9425
- Baldwin, J.E.¹ Mackenzie Turner, S.C.² Moloney, M.G.³

19
- 33751156001
- (s) Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872. Reviews:
- (1995) J. Org. Chem. , vol.60 , pp. 872
- Molander, G.A.¹ McKie, J.A.²

20
- 0007562550
- (t) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573.
- (1986) Tetrahedron , vol.42 , pp. 6573
- Kagan, H.B.¹ Namy, J.L.²

21
- 15144348917
- (u) Kagan, H. B. New J. Chem. 1990, 14, 53.
- (1990) New J. Chem. , vol.14 , pp. 53
- Kagan, H.B.¹

22
- 0010388170
- Hartley, H. R., Patai, S., Eds.; J. Wiley & Sons: New York
- (v) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, H. R., Patai, S., Eds.; J. Wiley & Sons: New York, 1989; Vol. 5, p 319.
- (1989) The Chemistry of the Metal-Carbon Bond , vol.5 , pp. 319
- Molander, G.A.¹

23
- 0000104215
- Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
- (w) Molander, G. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, p 251.
- (1991) Comprehensive Organic Synthesis , vol.1 , pp. 251
- Molander, G.A.¹

24
- 0342612489
- (x) Soderquist, J. A. Aldrichimica Acta 1991, 24, 14.
- (1991) Aldrichimica Acta , vol.24 , pp. 14
- Soderquist, J.A.¹

25
- 0010077452
- (y) Molander, G. A. Chem. Rev. 1992, 92, 29.
- (1992) Chem. Rev. , vol.92 , pp. 29
- Molander, G.A.¹

26
- 37049064853
- (a) Eakin, M.; Martin, J. J. Chem. Soc., Chem. Commun. 1965, 206.
- (1965) J. Chem. Soc., Chem. Commun. , pp. 206
- Eakin, M.¹ Martin, J.²

27
- 0000018066
- (b) Stork, G.; Malhorta, S.; Thompson, H.; Uchibayashi, M. J. Am. Chem. Soc. 1965, 87, 1148.
- (1965) J. Am. Chem. Soc. , vol.87 , pp. 1148
- Stork, G.¹ Malhorta, S.² Thompson, H.³ Uchibayashi, M.⁴

28
- 0000110934
- (c) Sowinski, A. F.; Whitesides, G. M. J. Org. Chem. 1979, 44, 2369.
- (1979) J. Org. Chem. , vol.44 , pp. 2369
- Sowinski, A.F.¹ Whitesides, G.M.²

29
- 33845556646
- (d) Pradhan, S. K.; Kadam, S. R.; Kolhe, J. N.; Radhakrishnan, T. V.; Shani, S. V.; Thaker, V. B. 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 Shani, S.V.⁵ Thaker, V.B.⁶

30
- 0000042023
- (e) Ikeda, T.; Yue, S.; Hutchinson, C. R. J. Org. Chem. 1985, 50, 5193.
- (1985) J. Org. Chem. , vol.50 , pp. 5193
- Ikeda, T.¹ Yue, S.² Hutchinson, C.R.³

31
- 33746402465
- (f) Corey, E. J.; Pyne, S. G. Tetrahedron Lett. 1983, 24, 2821.
- (1983) Tetrahedron Lett. , vol.24 , pp. 2821
- Corey, E.J.¹ Pyne, S.G.²

32
- 33947093235
- (a) Shono, T.; Nishiguchi, I.; Ohimizu, H.; Mitani, M. J. Am. Chem. Soc. 1978, 100, 545.
- (1978) J. Am. Chem. Soc. , vol.100 , pp. 545
- Shono, T.¹ Nishiguchi, I.² Ohimizu, H.³ Mitani, M.⁴

33
- 0000890281
- (b) Fox, D. P.; Little, R. D.; Baizer, M. M. J Org. Chem. 1985, 50, 2202.
- (1985) J Org. Chem. , vol.50 , pp. 2202
- Fox, D.P.¹ Little, R.D.² Baizer, M.M.³

34
- 0008478616
- (c) Kariv-Miller, E.; Mahachi, T. J. J. Org. Chem. 1986, 51, 1041.
- (1986) J. Org. Chem. , vol.51 , pp. 1041
- Kariv-Miller, E.¹ Mahachi, T.J.²

35
- 0000176763
- (d) Little, R. D.; Fox, D. P.; Hijfte, L. V.; Dannecker, R.; Sowell, G.; Wolin, R. L.; Moens, L.; Baizer, M. M. J. Org. Chem. 1988, 53, 2287.
- (1988) J. Org. Chem. , vol.53 , pp. 2287
- Little, R.D.¹ Fox, D.P.² Hijfte, L.V.³ Dannecker, R.⁴ Sowell, G.⁵ Wolin, R.L.⁶ Moens, L.⁷ Baizer, M.M.⁸

36
- 33845184473
- (e) Kariv-Miller, E.; Maeda, H.; Lombardo, P. J. Org. Chem. 1988, 54, 4022.
- (1988) J. Org. Chem. , vol.54 , pp. 4022
- Kariv-Miller, E.¹ Maeda, H.² Lombardo, P.³

37
- 46549103295
- (a) Belloti, D.; Cossy, J.; Pete, J. P.; Portella, C. Tetrahedron Lett. 1985, 26, 4591.
- (1985) Tetrahedron Lett. , vol.26 , pp. 4591
- Belloti, D.¹ Cossy, J.² Pete, J.P.³ Portella, C.⁴

38
- 33845375642
- (b) Belloti, D.; Cossy, J.; Pete, J. P.; Portella, C. J. Org. Chem. 1986, 51, 4196.
- (1986) J. Org. Chem. , vol.51 , pp. 4196
- Belloti, D.¹ Cossy, J.² Pete, J.P.³ Portella, C.⁴

39
- 0001178948
- (c) Cossy, J.; Belloti, D. Tetrahedron Lett. 1988, 29, 6113.
- (1988) Tetrahedron Lett. , vol.29 , pp. 6113
- Cossy, J.¹ Belloti, D.²

40
- 33845281959
- (a) Molander, G. A.; Etter, J. B.; Zinke, P. W. J. Am. Chem. Soc. 1987, 109, 453.
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 453
- Molander, G.A.¹ Etter, J.B.² Zinke, P.W.³

41
- 33845281219
- (b) Molander, G. A.; Etter, J. B. J. Am. Chem. Soc. 1987, 109, 6556.
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 6556
- Molander, G.A.¹ Etter, J.B.²

42
- 33845183971
- (a) Takai, K.; Nitta, K.; Fujimara, O.; Utimoto, K. J. Org. Chem. 1989, 54, 4732.
- (1989) J. Org. Chem. , vol.54 , pp. 4732
- Takai, K.¹ Nitta, K.² Fujimara, O.³ Utimoto, K.⁴

43
- 85034517625
- (b) Curran, D. P.; Fevig, T. L.; Totelben, M. J. Synlett 1990, 773.
- (1990) Synlett , pp. 773
- Curran, D.P.¹ Fevig, T.L.² Totelben, M.J.³

44
- 0000392657
- (c) Molander, G. A.; Hairing, L. S. J. Org. Chem. 1990, 55, 6171.
- (1990) J. Org. Chem. , vol.55 , pp. 6171
- Molander, G.A.¹ Hairing, L.S.²

45
- 0010530025
- (d) Curran, D. P.; Wolin, R. L. Synlett 1991, 317.
- (1991) Synlett , pp. 317
- Curran, D.P.¹ Wolin, R.L.²

46
- 0026015020
- (e) Baley, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649.
- (1991) Tetrahedron Lett. , vol.32 , pp. 6649
- Baley, R.A.¹ Motherwell, W.B.²

47
- 0000056566
- (f) Enholm, E. J.; Jiang, S.; Abboud, K. J. Org. Chem. 1993, 58, 4061.
- (1993) J. Org. Chem. , vol.58 , pp. 4061
- Enholm, E.J.¹ Jiang, S.² Abboud, K.³

48
- 0027208735
- (g) Yu, Y.; Lin, R.; Zhang, Y. Tetrahedron Lett. 1993, 34, 4547.
- (1993) Tetrahedron Lett. , vol.34 , pp. 4547
- Yu, Y.¹ Lin, R.² Zhang, Y.³

49
- 0001506856
- (h) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 3705
- Molander, G.A.¹ Harris, C.R.²

50
- 0029901507
- (i) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1996, 778, 4059.
- (1996) J. Am. Chem. Soc. , vol.778 , pp. 4059
- Molander, G.A.¹ Harris, C.R.²

51
- 2142715741
- (j) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
- (1996) Chem. Rev. , vol.96 , pp. 307
- Molander, G.A.¹ Harris, C.R.²

52
- 0032473838
- (k) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321.
- (1998) Tetrahedron , vol.54 , pp. 3321
- Molander, G.A.¹ Harris, C.R.²

53
- 0010291062
- (a) Sheenan, J. C.; O'Neill, R. C.; White, M. A. J. Am. Chem. Soc. 1950, 72, 3376. Reviews:
- (1950) J. Am. Chem. Soc. , vol.72 , pp. 3376
- Sheenan, J.C.¹ O'Neill, R.C.² White, M.A.³

54
- 33947483564
- (b) Finley, K. T. Chem. Rev. 1964, 64, 573,
- (1964) Chem. Rev. , vol.64 , pp. 573
- Finley, K.T.¹

55
- 0000871665
- J. Wiley & Sons: New York
- (c) Broomfield, J. J.; Owsley, D. C.; Nelke, J. N. In Organic Reactions; J. Wiley & Sons: New York, 1976; Vol. 23, p 259.
- (1976) Organic Reactions , vol.23 , pp. 259
- Broomfield, J.J.¹ Owsley, D.C.² Nelke, J.N.³

56
- 1542302615
- (a) Sheenan, J. C.; O'Neill, R. C. J. Am. Chem. Soc. 1950, 72, 4614.
- (1950) J. Am. Chem. Soc. , vol.72 , pp. 4614
- Sheenan, J.C.¹ O'Neill, R.C.²

57
- 15144349620
- (b) Sheenan, J. C.; Coderre, R. C. J. Am. Chem. Soc. 1953, 75, 3997.
- (1953) J. Am. Chem. Soc. , vol.75 , pp. 3997
- Sheenan, J.C.¹ Coderre, R.C.²

58
- 0000942347
- (c) Gutsche, C. D.; Tao, I. Y. C.; Kozma, J. J. Org. Chem. 1967, 32, 1782.
- (1967) J. Org. Chem. , vol.32 , pp. 1782
- Gutsche, C.D.¹ Tao, I.Y.C.² Kozma, J.³

59
- 15144351995
- Ph.D. Thesis, University of Colorado at Boulder
- Zinke, P. W. Ph.D. Thesis, University of Colorado at Boulder, 1987.
- (1987)
- Zinke, P.W.¹

60
- 33845184178
- (a) Kraus, G. A.; James, O. S. J. Org. Chem. 1989, 54, 77.
- (1989) J. Org. Chem. , vol.54 , pp. 77
- Kraus, G.A.¹ James, O.S.²

61
- 0030755324
- (b) Kraus, G. A.; Wan, Z. Tetrahedron Lett. 1997, 38, 6509.
- (1997) Tetrahedron Lett. , vol.38 , pp. 6509
- Kraus, G.A.¹ Wan, Z.²

62
- 0025014546
- (a) Shono, T.; Kise, N. Tetrahedron Lett. 1990, 31, 1303.
- (1990) Tetrahedron Lett. , vol.31 , pp. 1303
- Shono, T.¹ Kise, N.²

63
- 33751392297
- (b) Shono, T.; Kise, N.; Fujimoto, T.; Tominaga, N.; Monta, H. J. Org. Chem. 1992, 57, 7175.
- (1992) J. Org. Chem. , vol.57 , pp. 7175
- Shono, T.¹ Kise, N.² Fujimoto, T.³ Tominaga, N.⁴ Monta, H.⁵

64
- 0001367782
- J. Wiley & Sons: New York
- Molander, G. A. In Organic Reactions; J. Wiley & Sons: New York, 1994; Vol. 46, p 211.
- (1994) Organic Reactions , vol.46 , pp. 211
- Molander, G.A.¹

65
- 85022594998
- Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943.
- (1992) Synlett , pp. 943
- Curran, D.P.¹ Fevig, T.L.² Jasperse, C.P.³ Totleben, M.J.⁴

66
- 0001703044
- (a) Skene, W. G.; Scaiano, J. C.; Cozens, F. L. J. Org. Chem. 1996, 61, 7918.
- (1996) J. Org. Chem. , vol.61 , pp. 7918
- Skene, W.G.¹ Scaiano, J.C.² Cozens, F.L.³

67
- 0030889137
- (b) Ogawa, A.; Sumino, Y.; Nanke, T.; Ohya, S.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 2745.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 2745
- Ogawa, A.¹ Sumino, Y.² Nanke, T.³ Ohya, S.⁴ Sonoda, N.⁵ Hirao, T.⁶

68
- 0031509603
- (c) Ogawa, A.; Ohya, S.; Hirao, T. Chem. Lett. 1997, 275.
- (1997) Chem. Lett. , pp. 275
- Ogawa, A.¹ Ohya, S.² Hirao, T.³

69
- 0000934552
- (d) Molander, G. A.; Alonso-Alija, C. J. Org. Chem. 1998, 63, 4366.
- (1998) J. Org. Chem. , vol.63 , pp. 4366
- Molander, G.A.¹ Alonso-Alija, C.²

70
- 0032491024
- (e) Molander, G. A.; Sono, M. Tetrahedron 1998, 54, 9289.
- (1998) Tetrahedron , vol.54 , pp. 9289
- Molander, G.A.¹ Sono, M.²

71
- 0001938996
- Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485.
- (1987) Chem. Lett. , pp. 1485
- Inanaga, J.¹ Ishikawa, M.² Yamaguchi, M.³

72
- 0002433893
- Machrouhi, F.; Hamann, B.; Namy, J.-L.; Kagan, H. B. Synlett 1996, 633.
- (1996) Synlett , pp. 633
- Machrouhi, F.¹ Hamann, B.² Namy, J.-L.³ Kagan, H.B.⁴

73
- 0029953068
- Schwaebe, M.; Little, R. D. J. Org. Chem. 1996, 67, 3240.
- (1996) J. Org. Chem. , vol.67 , pp. 3240
- Schwaebe, M.¹ Little, R.D.²

74
- 33748366516
- (a) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073.
- (1981) Tetrahedron , vol.37 , pp. 3073
- Beckwith, A.L.J.¹

75
- 0000072258
- de-Mayo, R, Ed,; Academic Press: New York
- (b) Beckwith, A. L. J.; Ingold, K. U. Rearrangements in Ground and Excited States; de-Mayo, R, Ed,; Academic Press: New York, 1980; Vol. 1, p 161.
- (1980) Rearrangements in Ground and Excited States , vol.1 , pp. 161
- Beckwith, A.L.J.¹ Ingold, K.U.²

76
- 0003726028
- Wiley: New York
- Brown, H. C. Organic Syntheses via Boranes; Wiley: New York, 1975.
- (1975) Organic Syntheses Via Boranes
- Brown, H.C.¹

77
- 33947482604
- Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Ferrell, R. J. Am. Chem. Soc. 1963, 85, 207.
- (1963) J. Am. Chem. Soc. , vol.85 , pp. 207
- Stork, G.¹ Brizzolara, A.² Landesman, H.³ Szmuszkovicz, J.⁴ Ferrell, R.⁵

78
- 15144343745
- Hatzigrigoriou, E.; Roux-Schmitt, M.; Wartski, L.; SeydenPenne, J. J. Chem. Res. Miniprint 1985, 3575.
- (1985) J. Chem. Res. Miniprint , pp. 3575
- Hatzigrigoriou, E.¹ Roux-Schmitt, M.² Wartski, L.³ Seydenpenne, J.⁴

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