SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 133, Issue 36, 2011, Pages 14460-14466

Synthesis of cyclopentenols and cyclopentenones via nickel-catalyzed reductive cycloaddition

(4) Jenkins, Aireal D a Herath, Ananda a Song, Minsoo a Montgomery, John a

a UNIVERSITY OF MICHIGAN (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENONES; FIVE-MEMBERED RINGS; METALLACYCLIC INTERMEDIATES;

ACETYLENE;

CYCLOADDITION;

ALKYNE DERIVATIVE; CYCLOPENTENONE DERIVATIVE; CYCLOPENTOLATE; NICKEL;

ARTICLE; CATALYSIS; CYCLIZATION; CYCLOADDITION; OXIDATION REDUCTION REACTION; PROTON TRANSPORT; STOICHIOMETRY; SYNTHESIS;

EID: 80052579087 PISSN: 00027863 EISSN: 15205126 Source Type: Journal
DOI: 10.1021/ja206722t Document Type: Article

Times cited : (61)

References (65)

1
- 51049094424
- Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887-2902
- (2008) Chem. Rev. , vol.108 , pp. 2887-2902
- Stanley, L.M.¹ Sibi, M.P.²

2
- 35548985408
- Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247-12275
- (2007) Tetrahedron , vol.63 , pp. 12247-12275
- Nair, V.¹ Suja, T.D.²

3
- 11644296077
- Welker, M. E. Chem. Rev. 1992, 92, 97-112
- (1992) Chem. Rev. , vol.92 , pp. 97-112
- Welker, M.E.¹

4
- 84985502069
- Trost, B. M. Angew. Chem., Int. Ed. 1986, 25, 1-20
- (1986) Angew. Chem., Int. Ed. , vol.25 , pp. 1-20
- Trost, B.M.¹

5
- 0001500173
- Nakamura, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 344, 111-129
- (2002) Adv. Synth. Catal. , vol.344 , pp. 111-129
- Nakamura, I.¹ Yamamoto, Y.²

6
- 0034829401
- Davies, H. M. L.; Xiang, B.; Kong, N.; Stafford, D. G. J. Am. Chem. Soc. 2001, 123, 7461-7462
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 7461-7462
- Davies, H.M.L.¹ Xiang, B.² Kong, N.³ Stafford, D.G.⁴

7
- 0001070917
- Davies, H. M. L.; Hu, B. B.; Saikali, E.; Bruzinski, P. R. J. Org. Chem. 1994, 59, 4535-4541
- (1994) J. Org. Chem. , vol.59 , pp. 4535-4541
- Davies, H.M.L.¹ Hu, B.B.² Saikali, E.³ Bruzinski, P.R.⁴

8
- 36448955053
- Barluenga, J.; Barrio, P.; Riesgo, L.; Lopez, L. A.; Tomas, M. J. Am. Chem. Soc. 2007, 129, 14422-14426
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 14422-14426
- Barluenga, J.¹ Barrio, P.² Riesgo, L.³ Lopez, L.A.⁴ Tomas, M.⁵

9
- 28044450635
- Pohlhaus, P. D.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 16014-16015
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 16014-16015
- Pohlhaus, P.D.¹ Johnson, J.S.²

10
- 77956450521
- Lebold, T. P.; Kerr, M. A. Pure Appl. Chem. 2010, 82, 1797-1812
- (2010) Pure Appl. Chem. , vol.82 , pp. 1797-1812
- Lebold, T.P.¹ Kerr, M.A.²

11
- 0037884930
- Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196
- (2003) Chem. Rev. , vol.103 , pp. 1151-1196
- Reissig, H.-U.¹ Zimmer, R.²

12
- 0001105181
- Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300-3302
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 3300-3302
- Feldman, K.S.¹ Romanelli, A.L.² Ruckle, R.E.³ Miller, R.F.⁴

13
- 54749100732
- Qi, X.; Ready, J. M. Angew. Chem., Int. Ed. 2008, 47, 7068-7070
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 7068-7070
- Qi, X.¹ Ready, J.M.²

14
- 33646463634
- Liu, L.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 5348-5349
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 5348-5349
- Liu, L.¹ Montgomery, J.²

15
- 33646464559
- Ogoshi, S.; Nagata, M.; Kurosawa, H. J. Am. Chem. Soc. 2006, 128, 5350-5351
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 5350-5351
- Ogoshi, S.¹ Nagata, M.² Kurosawa, H.³

16
- 0002307453
- The Pauson-Khand Cycloaddition Reaction for Synthesis of Cyclopentenones
- Schore, N. E. The Pauson-Khand Cycloaddition Reaction for Synthesis of Cyclopentenones Org. React. 1991, 40, 1-90
- (1991) Org. React. , vol.40 , pp. 1-90
- Schore, N.E.¹

17
- 0034686072
- Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283
- (2000) Tetrahedron , vol.56 , pp. 3263-3283
- Brummond, K.M.¹ Kent, J.L.²

18
- 0034697670
- Trost, B. M.; Brown, R. E.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 5877-5878
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 5877-5878
- Trost, B.M.¹ Brown, R.E.² Toste, F.D.³

19
- 63149091762
- Koyama, I.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2009, 131, 1350-1351
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 1350-1351
- Koyama, I.¹ Kurahashi, T.² Matsubara, S.³

20
- 0343778881
- For a review of allylsilane [3 + 2] cycloadditions, see
- For a review of allylsilane [3 + 2] cycloadditions, see: Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316
- (1995) Chem. Rev. , vol.95 , pp. 1293-1316
- Masse, C.E.¹ Panek, J.S.²

21
- 0007930541
- Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604-1606
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 1604-1606
- Danheiser, R.L.¹ Carini, D.J.² Basak, A.³

22
- 33751391619
- Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094-6097
- (1992) J. Org. Chem. , vol.57 , pp. 6094-6097
- Danheiser, R.L.¹ Dixon, B.R.² Gleason, R.W.³

23
- 5144220014
- For a review of phosphine-based organocatalytic [3 + 2] cycloadditions
- For a review of phosphine-based organocatalytic [3 + 2] cycloadditions, see: Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035-1050
- (2004) Adv. Synth. Catal. , vol.346 , pp. 1035-1050
- Methot, J.L.¹ Roush, W.R.²

24
- 7744232978
- Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370-14371
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 14370-14371
- Sohn, S.S.¹ Rosen, E.L.² Bode, J.W.³

25
- 33751156723
- Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 2906-2908
- (1995) J. Org. Chem. , vol.60 , pp. 2906-2908
- Zhang, C.¹ Lu, X.²

26
- 0037414272
- Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682-3683
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 3682-3683
- Wang, J.-C.¹ Ng, S.-S.² Krische, M.J.³

27
- 33750476310
- A portion of this work has previously been described
- A portion of this work has previously been described: Herath, A.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 14030-14031
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 14030-14031
- Herath, A.¹ Montgomery, J.²

28
- 34247165160
- Chang, H. T.; Jayanth, T. T.; Cheng, C. H. J. Am. Chem. Soc. 2007, 129, 4166-4167
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 4166-4167
- Chang, H.T.¹ Jayanth, T.T.² Cheng, C.H.³

29
- 0029823460
- Suzuki, K.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1996, 118, 8729-8730
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 8729-8730
- Suzuki, K.¹ Urabe, H.² Sato, F.³

30
- 0030697490
- Urabe, H.; Suzuki, K.; Sato, F. J. Am. Chem. Soc. 1997, 119, 10014-10027
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 10014-10027
- Urabe, H.¹ Suzuki, K.² Sato, F.³

31
- 70450206823
- Williams, V. M.; Kong, J. R.; Ko, B. J.; Mantri, Y.; Brodbelt, J. S.; Baik, M.-H.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 16054-16062
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 16054-16062
- Williams, V.M.¹ Kong, J.R.² Ko, B.J.³ Mantri, Y.⁴ Brodbelt, J.S.⁵ Baik, M.-H.⁶ Krische, M.J.⁷

32
- 68949086065
- Schomaker, J. M.; Toste, F. D.; Bergman, R. G. Org. Lett. 2009, 11, 3698-3700
- (2009) Org. Lett. , vol.11 , pp. 3698-3700
- Schomaker, J.M.¹ Toste, F.D.² Bergman, R.G.³

33
- 33845373571
- Molander, G. A.; Shubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683-4685
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 4683-4685
- Molander, G.A.¹ Shubert, D.C.²

34
- 0030948010
- Nakamura, H.; Aoyagi, K.; Singaram, B.; Cai, J.; Nemoto, H.; Yamamoto, Y. Angew. Chem., Int. Ed. 1997, 36, 367-369
- (1997) Angew. Chem., Int. Ed. , vol.36 , pp. 367-369
- Nakamura, H.¹ Aoyagi, K.² Singaram, B.³ Cai, J.⁴ Nemoto, H.⁵ Yamamoto, Y.⁶

35
- 0000467378
- Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784-7785
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 7784-7785
- Enholm, E.J.¹ Kinter, K.S.²

36
- 0002937546
- Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4-5
- (1996) J. Org. Chem. , vol.61 , pp. 4-5
- Hays, D.S.¹ Fu, G.C.²

37
- 0000757165
- Savchenko, A. V.; Montgomery, J. J. Org. Chem. 1996, 61, 1562-1563
- (1996) J. Org. Chem. , vol.61 , pp. 1562-1563
- Savchenko, A.V.¹ Montgomery, J.²

38
- 0041340694
- Kulinkovich, O. G. Chem. Rev. 2003, 103, 2597-2632
- (2003) Chem. Rev. , vol.103 , pp. 2597-2632
- Kulinkovich, O.G.¹

39
- 0029991524
- Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198-4199
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 4198-4199
- Lee, J.¹ Kim, H.² Cha, J.K.³

40
- 0030858681
- For examples of oxidative cycloadditions
- For examples of oxidative cycloadditions: Snider, B. B.; Han, L.; Xie, C. J. Org. Chem. 1997, 62, 6978-6984
- (1997) J. Org. Chem. , vol.62 , pp. 6978-6984
- Snider, B.B.¹ Han, L.² Xie, C.³

41
- 0034686737
- Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2000, 122, 6775-6776
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 6775-6776
- Chowdhury, S.K.¹ Amarasinghe, K.K.D.² Heeg, M.J.³ Montgomery, J.⁴

42
- 0035809288
- Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370-372
- (2001) Organometallics , vol.20 , pp. 370-372
- Amarasinghe, K.K.D.¹ Chowdhury, S.K.² Heeg, M.J.³ Montgomery, J.⁴

43
- 0242330786
- Mahandru, G. M.; Skauge, A. R. L.; Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2003, 125, 13481-13485
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 13481-13485
- Mahandru, G.M.¹ Skauge, A.R.L.² Chowdhury, S.K.³ Amarasinghe, K.K.D.⁴ Heeg, M.J.⁵ Montgomery, J.⁶

44
- 0035476966
- Kimura, M.; Ezoe, A.; Tanaka, S.; Tamaru, Y. Angew. Chem., Int. Ed. 2001, 40, 3600-3602
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3600-3602
- Kimura, M.¹ Ezoe, A.² Tanaka, S.³ Tamaru, Y.⁴

45
- 0037471214
- Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364-1367
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 1364-1367
- Patel, S.J.¹ Jamison, T.F.²

46
- 70450194575
- Li, W.; Herath, A.; Montgomery, J. J. Am. Chem. Soc. 2009, 131, 17024-17029
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 17024-17029
- Li, W.¹ Herath, A.² Montgomery, J.³

47
- 34848890628
- Herath, A.; Thompson, B. B.; Montgomery, J. J. Am. Chem. Soc. 2007, 129, 8712-8713
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 8712-8713
- Herath, A.¹ Thompson, B.B.² Montgomery, J.³

48
- 4544323639
- Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890-3908
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3890-3908
- Montgomery, J.¹

49
- 0037151634
- Wang, C.-C.; Lin, P.-S.; Cheng, C.-H. J. Am. Chem. Soc. 2002, 124, 9696-9697
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 9696-9697
- Wang, C.-C.¹ Lin, P.-S.² Cheng, C.-H.³

50
- 34848900461
- Chang, H.-T.; Jayanth, T. T.; Wang, C.-C.; Cheng, C.-H. J. Am. Chem. Soc. 2007, 129, 12032-12041
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 12032-12041
- Chang, H.-T.¹ Jayanth, T.T.² Wang, C.-C.³ Cheng, C.-H.⁴

51
- 57149129735
- Jeganmohan, M.; Cheng, C.-H. Chem.-Eur. J. 2008, 14, 10876-10886
- (2008) Chem.-Eur. J. , vol.14 , pp. 10876-10886
- Jeganmohan, M.¹ Cheng, C.-H.²

52
- 35948968063
- Moslin, R. M.; Miller-Moslin, K.; Jamison, T. F. Chem. Commun. 2007, 4441-4449
- (2007) Chem. Commun. , pp. 4441-4449
- Moslin, R.M.¹ Miller-Moslin, K.² Jamison, T.F.³

53
- 58249100133
- Bower, J. F.; Kim, I. S.; Patman, R. L.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 34-46
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 34-46
- Bower, J.F.¹ Kim, I.S.² Patman, R.L.³ Krische, M.J.⁴

54
- 38049062493
- Skukcas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394-1401
- (2007) Acc. Chem. Res. , vol.40 , pp. 1394-1401
- Skukcas, E.¹ Ngai, M.-Y.² Komanduri, V.³ Krische, M.J.⁴

55
- 74549172880
- Reichard, H. A.; McLaughlin, M.; Chen, M. Z.; Micalizio, G. C. Eur. J. Org. Chem. 2010, 391-409
- (2010) Eur. J. Org. Chem. , pp. 391-409
- Reichard, H.A.¹ McLaughlin, M.² Chen, M.Z.³ Micalizio, G.C.⁴

56
- 2942635094
- Matsunaga, S.; Kinoshita, T.; Okada, S.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 7559-7570
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 7559-7570
- Matsunaga, S.¹ Kinoshita, T.² Okada, S.³ Harada, S.⁴ Shibasaki, M.⁵

57
- 77953076639
- Malik, H. A.; Sormunen, G. J.; Montgomery, J. J. Am. Chem. Soc. 2010, 132, 6304-6305
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 6304-6305
- Malik, H.A.¹ Sormunen, G.J.² Montgomery, J.³

58
- 0001633976
- Chen, K.-M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem. Lett. 1987, 1923-1926
- (1987) Chem. Lett. , pp. 1923-1926
- Chen, K.-M.¹ Gunderson, K.G.² Hardtmann, G.E.³ Prasad, K.⁴ Repic, O.⁵ Shapiro, M.J.⁶

59
- 4944241519
- Hratchian, H. P.; Chowdhury, S. K.; Gutierrez-Garcia, V. M.; Amarasinghe, K. K. D.; Heeg, M. J.; Schlegel, H. B.; Montgomery, J. Organometallics 2004, 23, 4636-4646
- (2004) Organometallics , vol.23 , pp. 4636-4646
- Hratchian, H.P.¹ Chowdhury, S.K.² Gutierrez-Garcia, V.M.³ Amarasinghe, K.K.D.⁴ Heeg, M.J.⁵ Schlegel, H.B.⁶ Montgomery, J.⁷

60
- 25144460599
- Ogoshi, S.; Ueta, M.; Arai, T.; Kurosawa, H. J. Am. Chem. Soc. 2005, 127, 12810-12811
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 12810-12811
- Ogoshi, S.¹ Ueta, M.² Arai, T.³ Kurosawa, H.⁴

61
- 67650514044
- McCarren, P. R.; Liu, P.; Cheong, P. H.-Y.; Jamison, T. F.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 6654-6655
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 6654-6655
- McCarren, P.R.¹ Liu, P.² Cheong, P.H.-Y.³ Jamison, T.F.⁴ Houk, K.N.⁵

62
- 40149091315
- Herath, A.; Li, W.; Montgomery, J. J. Am. Chem. Soc. 2008, 130, 469-471
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 469-471
- Herath, A.¹ Li, W.² Montgomery, J.³

63
- 72249106677
- Ni, Y.; Kassab, R. M.; Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 2009, 131, 17714-17718
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 17714-17718
- Ni, Y.¹ Kassab, R.M.² Chevliakov, M.V.³ Montgomery, J.⁴

64
- 79958217721
- El Douhaibi, A. S.; Kassab, R. M.; Song, M.; Montgomery, J. Chem.-Eur. J. 2011, 17, 6326-6329
- (2011) Chem.-Eur. J. , vol.17 , pp. 6326-6329
- El Douhaibi, A.S.¹ Kassab, R.M.² Song, M.³ Montgomery, J.⁴

65
- 0033537060
- Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139-11143
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 11139-11143
- Chevliakov, M.V.¹ Montgomery, J.²

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