SCOPUS 정보 검색 플랫폼

Chemistry - A European Journal

Volumn 18, Issue 36, 2012, Pages 11214-11218

Enantioselective nickel-catalyzed Michael additions of azaarylacetates and acetamides to nitroalkenes

(2) Fallan, Charlene a Lam, Hon Wai a

a UNIVERSITY OF EDINBURGH (United Kingdom)

Author keywords

asymmetric catalysis; enantioselectivity; Michael addition; nickel; nitroalkenes

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; AZAARENES; ENANTIOSELECTIVE; ENANTIOSELECTIVE MICHAEL ADDITION; MICHAEL ADDITIONS; NITROALKENES;

ADDITION REACTIONS; CATALYSIS; MOLECULAR SIEVES; NICKEL; NICKEL COMPOUNDS;

ENANTIOSELECTIVITY;

ACETAMIDE DERIVATIVE; ACETIC ACID DERIVATIVE; ALKENE; HETEROCYCLIC COMPOUND; NICKEL; NITRO DERIVATIVE; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETAMIDES; ACETATES; ALKENES; AZA COMPOUNDS; CATALYSIS; MOLECULAR STRUCTURE; NICKEL; NITRO COMPOUNDS; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 84865487224 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201202093 Document Type: Article

Times cited : (45)

References (61)

1
- 68049108506
- L. Rupnicki, A. Saxena, H. W. Lam, J. Am. Chem. Soc. 2009, 131, 10386-10387
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 10386-10387
- Rupnicki, L.¹ Saxena, A.² Lam, H.W.³

2
- 77958067774
- G. Pattison, G. Piraux, H. W. Lam, J. Am. Chem. Soc. 2010, 132, 14373-14375.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 14373-14375
- Pattison, G.¹ Piraux, G.² Lam, H.W.³

3
- 0032510191
- I. N. Houpis, J. Lee, I. Dorziotis, A. Molina, B. Reamer, R. P. Volante, P. J. Reider, Tetrahedron 1998, 54, 1185-1195
- (1998) Tetrahedron , vol.54 , pp. 1185-1195
- Houpis, I.N.¹ Lee, J.² Dorziotis, I.³ Molina, A.⁴ Reamer, B.⁵ Volante, R.P.⁶ Reider, P.J.⁷

4
- 78650322008
- A. Baschieri, L. Bernardi, A. Ricci, S. Suresh, M. F. A. Adamo, Angew. Chem. 2009, 121, 9506-9509
- (2009) Angew. Chem. , vol.121 , pp. 9506-9509
- Baschieri, A.¹ Bernardi, L.² Ricci, A.³ Suresh, S.⁴ Adamo, M.F.A.⁵

5
- 72949097675
- Angew. Chem. Int. Ed. 2009, 48, 9342-9345
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9342-9345

6
- 79955793513
- H.-W. Sun, Y.-H. Liao, Z.-J. Wu, H.-Y. Wang, X.-M. Zhang, W.-C. Yuan, Tetrahedron 2011, 67, 3991-3996.
- (2011) Tetrahedron , vol.67 , pp. 3991-3996
- Sun, H.-W.¹ Liao, Y.-H.² Wu, Z.-J.³ Wang, H.-Y.⁴ Zhang, X.-M.⁵ Yuan, W.-C.⁶

7
- 84861396390
- For enantioselective copper-catalyzed reductive couplings of alkenylazaarenes with ketones, see:, A. Saxena, B. Choi, H. W. Lam, J. Am. Chem. Soc. 2012, 134, 8428-8431.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 8428-8431
- Saxena, A.¹ Choi, B.² Lam, H.W.³

8
- 54849431595
- B. M. Trost, D. A. Thaisrivongs, J. Am. Chem. Soc. 2008, 130, 14092-14093
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14092-14093
- Trost, B.M.¹ Thaisrivongs, D.A.²

9
- 69349099076
- B. M. Trost, D. A. Thaisrivongs, J. Am. Chem. Soc. 2009, 131, 12056-12057
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 12056-12057
- Trost, B.M.¹ Thaisrivongs, D.A.²

10
- 80051592008
- B. M. Trost, D. A. Thaisrivongs, J. Hartwig, J. Am. Chem. Soc. 2011, 133, 12439-12441.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 12439-12441
- Trost, B.M.¹ Thaisrivongs, D.A.² Hartwig, J.³

11
- 0002172830
- H. Hamana, T. Sugasawa, Chem. Lett. 1983, 333-336
- (1983) Chem. Lett. , pp. 333-336
- Hamana, H.¹ Sugasawa, T.²

12
- 0013356319
- H. Hamana, T. Sugasawa, Chem. Lett. 1984, 1591-1594.
- (1984) Chem. Lett. , pp. 1591-1594
- Hamana, H.¹ Sugasawa, T.²

13
- 77949833074
- B. Qian, S. Guo, J. Shao, Q. Zhu, L. Yang, C. Xia, H. Huang, J. Am. Chem. Soc. 2010, 132, 3650-3651
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 3650-3651
- Qian, B.¹ Guo, S.² Shao, J.³ Zhu, Q.⁴ Yang, L.⁵ Xia, C.⁶ Huang, H.⁷

14
- 78650321875
- B. Qian, S. Guo, C. Xia, H. Huang, Adv. Synth. Catal. 2010, 352, 3195-3200
- (2010) Adv. Synth. Catal. , vol.352 , pp. 3195-3200
- Qian, B.¹ Guo, S.² Xia, C.³ Huang, H.⁴

15
- 79956148086
- B. Qian, P. Xie, Y. Xie, H. Huang, Org. Lett. 2011, 13, 2580-2583
- (2011) Org. Lett. , vol.13 , pp. 2580-2583
- Qian, B.¹ Xie, P.² Xie, Y.³ Huang, H.⁴

16
- 79952150244
- M. Rueping, N. Tolstoluzhsky, Org. Lett. 2011, 13, 1095-1097
- (2011) Org. Lett. , vol.13 , pp. 1095-1097
- Rueping, M.¹ Tolstoluzhsky, N.²

17
- 79953174314
- H. Komai, T. Yoshino, S. Matsunaga, M. Kanai, Org. Lett. 2011, 13, 1706-1709.
- (2011) Org. Lett. , vol.13 , pp. 1706-1709
- Komai, H.¹ Yoshino, T.² Matsunaga, S.³ Kanai, M.⁴

18
- 80051726726
- Y. Yan, K. Xu, Y. Fang, Z. Wang, J. Org. Chem. 2011, 76, 6849-6855.
- (2011) J. Org. Chem. , vol.76 , pp. 6849-6855
- Yan, Y.¹ Xu, K.² Fang, Y.³ Wang, Z.⁴

19
- 41449099894
- L.-C. Campeau, D. J. Schipper, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 3266-3267
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 3266-3267
- Campeau, L.-C.¹ Schipper, D.J.² Fagnou, K.³

20
- 62049083990
- D. J. Schipper, L.-C. Campeau, K. Fagnou, Tetrahedron 2009, 65, 3155-3164
- (2009) Tetrahedron , vol.65 , pp. 3155-3164
- Schipper, D.J.¹ Campeau, L.-C.² Fagnou, K.³

21
- 78650368300
- P. M. Burton, J. A. Morris, Org. Lett. 2010, 12, 5359-5361
- (2010) Org. Lett. , vol.12 , pp. 5359-5361
- Burton, P.M.¹ Morris, J.A.²

22
- 79955381933
- G. Song, Y. Su, X. Gong, K. Han, X. Li, Org. Lett. 2011, 13, 1968-1971.
- (2011) Org. Lett. , vol.13 , pp. 1968-1971
- Song, G.¹ Su, Y.² Gong, X.³ Han, K.⁴ Li, X.⁵

23
- 79951850684
- S. Vera, Y. Liu, M. Marigo, E. C. Escudero-Adán, P. Melchiorre, Synlett 2011, 489-494.
- (2011) Synlett , pp. 489-494
- Vera, S.¹ Liu, Y.² Marigo, M.³ Escudero-Adán, E.C.⁴ Melchiorre, P.⁵

24
- 77955688261
- M. B. n. Cid, S. Duce, S. Morales, E. Rodrigo, J. L. G. a. Ruano, Org. Lett. 2010, 12, 3586-3589.
- (2010) Org. Lett. , vol.12 , pp. 3586-3589
- Duce, S.¹ Morales, S.² Rodrigo, E.³

25
- 0347727821
- H. Beyer, W. Lässig, G. Schudy, Chem. Ber. 1957, 90, 592-598
- (1957) Chem. Ber. , vol.90 , pp. 592-598
- Beyer, H.¹ Lässig, W.² Schudy, G.³

26
- 0000032454
- W. M. Odijk, G. J. Koomen, Tetrahedron 1985, 41, 1893-1904
- (1985) Tetrahedron , vol.41 , pp. 1893-1904
- Odijk, W.M.¹ Koomen, G.J.²

27
- 52449127169
- M. Jeanty, F. Suzenet, G. Guillaumet, J. Org. Chem. 2008, 73, 7390-7393
- (2008) J. Org. Chem. , vol.73 , pp. 7390-7393
- Jeanty, M.¹ Suzenet, F.² Guillaumet, G.³

28
- 65449173132
- S. H. Kim, H. S. Lee, S. H. Kim, J. N. Kim, Tetrahedron Lett. 2009, 50, 3038-3041.
- (2009) Tetrahedron Lett. , vol.50 , pp. 3038-3041
- Kim, S.H.¹ Lee, H.S.² Kim, S.H.³ Kim, J.N.⁴

29
- 33845375521
- A. G. M. Barrett, G. G. Graboski, Chem. Rev. 1986, 86, 751-762
- (1986) Chem. Rev. , vol.86 , pp. 751-762
- Barrett, A.G.M.¹ Graboski, G.G.²

30
- 12044259240
- A. G. M. Barrett, Chem. Soc. Rev. 1991, 20, 95-127
- (1991) Chem. Soc. Rev. , vol.20 , pp. 95-127
- Barrett, A.G.M.¹

31
- 0036089366
- O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877-1894.
- (2002) Eur. J. Org. Chem. , pp. 1877-1894
- Berner, O.M.¹ Tedeschi, L.² Enders, D.³

32
- 0142072631
- T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc. 2003, 125, 12672-12673
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 12672-12673
- Okino, T.¹ Hoashi, Y.² Takemoto, Y.³

33
- 4043154104
- H. Li, Y. Wang, L. Tang, L. Deng, J. Am. Chem. Soc. 2004, 126, 9906-9907
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 9906-9907
- Li, H.¹ Wang, Y.² Tang, L.³ Deng, L.⁴

34
- 11844302258
- T. Okino, Y. Hoashi, T. Furukawa, X. Xu, Y. Takemoto, J. Am. Chem. Soc. 2005, 127, 119-125
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 119-125
- Okino, T.¹ Hoashi, Y.² Furukawa, T.³ Xu, X.⁴ Takemoto, Y.⁵

35
- 18844451481
- H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman, L. Deng, Angew. Chem. 2005, 117, 107-110
- (2005) Angew. Chem. , vol.117 , pp. 107-110
- Li, H.¹ Wang, Y.² Tang, L.³ Wu, F.⁴ Liu, X.⁵ Guo, C.⁶ Foxman, B.M.⁷ Deng, L.⁸

36
- 33745370454
- Angew. Chem. Int. Ed. 2005, 44, 105-108
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 105-108

37
- 25444473664
- J. Ye, D. J. Dixon, P. S. Hynes, Chem. Commun. 2005, 4481-4483
- (2005) Chem. Commun. , pp. 4481-4483
- Ye, J.¹ Dixon, D.J.² Hynes, P.S.³

38
- 32044439817
- S. H. McCooey, S. J. Connon, Angew. Chem. 2005, 117, 6525-6528
- (2005) Angew. Chem. , vol.117 , pp. 6525-6528
- McCooey, S.H.¹ Connon, S.J.²

39
- 26844450640
- Angew. Chem. Int. Ed. 2005, 44, 6367-6370
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 6367-6370

40
- 32244444791
- M. Terada, H. Ube, Y. Yaguchi, J. Am. Chem. Soc. 2006, 128, 1454-1455
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 1454-1455
- Terada, M.¹ Ube, H.² Yaguchi, Y.³

41
- 53849136278
- J. M. Andrés, R. Manzano, R. Pedrosa, Chem. Eur. J. 2008, 14, 5116-5119
- (2008) Chem. Eur. J. , vol.14 , pp. 5116-5119
- Andrés, J.M.¹ Manzano, R.² Pedrosa, R.³

42
- 51649096678
- W.-M. Zhou, H. Liu, D.-M. Du, Org. Lett. 2008, 10, 2817-2820
- (2008) Org. Lett. , vol.10 , pp. 2817-2820
- Zhou, W.-M.¹ Liu, H.² Du, D.-M.³

43
- 64349116913
- Y.-n. Xuan, S.-z. Nie, L.-t. Dong, J.-m. Zhang, M. Yan, Org. Lett. 2009, 11, 1583-1586
- (2009) Org. Lett. , vol.11 , pp. 1583-1586
- Yan, M.¹

44
- 67650086613
- H. Li, L. Zu, H. Xie, W. Wang, Synthesis 2009, 1525-1530.
- (2009) Synthesis , pp. 1525-1530
- Li, H.¹ Zu, L.² Xie, H.³ Wang, W.⁴

45
- 0033520797
- J. Ji, D. M. Barnes, J. Zhang, S. A. King, S. J. Wittenberger, H. E. Morton, J. Am. Chem. Soc. 1999, 121, 10215-10216
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 10215-10216
- Ji, J.¹ Barnes, D.M.² Zhang, J.³ King, S.A.⁴ Wittenberger, S.J.⁵ Morton, H.E.⁶

46
- 0037032313
- D. M. Barnes, J. Ji, M. G. Fickes, M. A. Fitzgerald, S. A. King, H. E. Morton, F. A. Plagge, M. Preskill, S. H. Wagaw, S. J. Wittenberger, J. Zhang, J. Am. Chem. Soc. 2002, 124, 13097-13105
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 13097-13105
- Barnes, D.M.¹ Ji, J.² Fickes, M.G.³ Fitzgerald, M.A.⁴ King, S.A.⁵ Morton, H.E.⁶ Plagge, F.A.⁷ Preskill, M.⁸ Wagaw, S.H.⁹ Wittenberger, S.J.¹⁰ Zhang, J.¹¹

47
- 4544301719
- M. Watanabe, A. Ikagawa, H. Wang, K. Murata, T. Ikariya, J. Am. Chem. Soc. 2004, 126, 11148-11149
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 11148-11149
- Watanabe, M.¹ Ikagawa, A.² Wang, H.³ Murata, K.⁴ Ikariya, T.⁵

48
- 22244487612
- D. A. Evans, D. Seidel, J. Am. Chem. Soc. 2005, 127, 9958-9959
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 9958-9959
- Evans, D.A.¹ Seidel, D.²

49
- 35048868490
- D. A. Evans, S. Mito, D. Seidel, J. Am. Chem. Soc. 2007, 129, 11583-11592
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 11583-11592
- Evans, D.A.¹ Mito, S.² Seidel, D.³

50
- 77953688004
- W.-Y. Chen, L. Ouyang, R.-Y. Chen, X.-S. Li, Tetrahedron Lett. 2010, 51, 3972-3974.
- (2010) Tetrahedron Lett. , vol.51 , pp. 3972-3974
- Chen, W.-Y.¹ Ouyang, L.² Chen, R.-Y.³ Li, X.-S.⁴

51
- 77950262715
- For application of a similar complex in the catalytic enantioselective addition of α-ketoesters to nitroalkenes, see:, A. Nakamura, S. Lectard, D. Hashizume, Y. Hamashima, M. Sodeoka, J. Am. Chem. Soc. 2010, 132, 4036-4037.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 4036-4037
- Nakamura, A.¹ Lectard, S.² Hashizume, D.³ Hamashima, Y.⁴ Sodeoka, M.⁵

52
- 0000445631
- The ee values were slightly lower in the absence of 3 Å molecular sieves. For a review of the effects of additives in asymmetric catalysis, see:, E. M. Vogl, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 1672-1680
- (1999) Angew. Chem. , vol.111 , pp. 1672-1680
- Vogl, E.M.¹ Gröger, H.² Shibasaki, M.³

53
- 0345711474
- Angew. Chem. Int. Ed. 1999, 38, 1570-1577.
- (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1570-1577

54
- 33845471613
- D. A. Evans, M. D. Ennis, T. Le, N. Mandel, G. Mandel, J. Am. Chem. Soc. 1984, 106, 1154-1156
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 1154-1156
- Evans, D.A.¹ Ennis, M.D.² Le, T.³ Mandel, N.⁴ Mandel, G.⁵

55
- 0026553351
- D. A. Evans, H. P. Ng, J. S. Clark, D. L. Rieger, Tetrahedron 1992, 48, 2127-2142
- (1992) Tetrahedron , vol.48 , pp. 2127-2142
- Evans, D.A.¹ Ng, H.P.² Clark, J.S.³ Rieger, D.L.⁴

56
- 67649534202
- M. Ogata, T. Yoshimura, H. Fujii, Y. Ito, T. Katsuki, Synlett 1993, 728-730
- (1993) Synlett , pp. 728-730
- Ogata, M.¹ Yoshimura, T.² Fujii, H.³ Ito, Y.⁴ Katsuki, T.⁵

57
- 0029014408
- J. Bartroli, E. Turmo, J. Belloc, J. Forn, J. Org. Chem. 1995, 60, 3000-3012
- (1995) J. Org. Chem. , vol.60 , pp. 3000-3012
- Bartroli, J.¹ Turmo, E.² Belloc, J.³ Forn, J.⁴

58
- 0035979030
- A. B. Smith, B. M. Brandt, Org. Lett. 2001, 3, 1685-1688
- (2001) Org. Lett. , vol.3 , pp. 1685-1688
- Smith, A.B.¹ Brandt, B.M.²

59
- 67649506357
- Q. Liu, T. Rovis, Org. Lett. 2009, 11, 2856-2859.
- (2009) Org. Lett. , vol.11 , pp. 2856-2859
- Liu, Q.¹ Rovis, T.²

60
- 84865449910
- For application of 2 in complex total synthesis, see
- For application of 2 in complex total synthesis, see:, J. Chen, J. Chen, Y. Xie, H. Zhang, Angew. Chem. 2012, 124, 1048-1051
- (2012) Angew. Chem. , vol.124 , pp. 1048-1051
- Chen, J.¹ Chen, J.² Xie, Y.³ Zhang, H.⁴

61
- 84862958665
- Angew. Chem. Int. Ed. 2012, 51, 1024-1027.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1024-1027

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.