SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 51, Issue 44, 2012, Pages 11101-11104

Diastereoselective metal-catalyzed synthesis of C-aryl and C-vinyl glycosides

(7) Nicolas, Lionel a Angibaud, Patrick b Stansfield, Ian b Bonnet, Pascal b Meerpoel, Lieven b Reymond, Sébastien a Cossy, Janine a

a CNRS (France)

b JANSSEN RESEARCH AND DEVELOPMENT (Belgium)

Author keywords

C glycosides; cobalt; cross coupling; diastereoselectivity; Grignard reagent

Indexed keywords

ACETYLACETONATES; C-GLYCOSIDES; CROSS-COUPLINGS; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; GRIGNARD REAGENT; TETRAMETHYLETHYLENEDIAMINE;

CATALYSIS; COBALT; GLUCOSE; STEREOSELECTIVITY;

CATALYST SELECTIVITY;

COBALT; GLYCOSIDE; IRON; ORGANOMETALLIC COMPOUND;

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

CATALYSIS; COBALT; GLYCOSIDES; IRON; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 84867824929 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201204786 Document Type: Article

Times cited : (150)

References (68)

1
- 75349084278
- J. Stanbasky, M. Hocek, P. Kosovsky, Chem. Rev. 2009, 109, 6729-6764
- (2009) Chem. Rev. , vol.109 , pp. 6729-6764
- Stanbasky, J.¹ Hocek, M.² Kosovsky, P.³

2
- 3142736550
- Q. Wu, C. Simons, Synthesis 2004, 1533-1553
- (2004) Synthesis , pp. 1533-1553
- Wu, Q.¹ Simons, C.²

3
- 29444453052
- P. G. Hultin, Curr. Top. Med. Chem. 2005, 5, 1299-1331
- (2005) Curr. Top. Med. Chem. , vol.5 , pp. 1299-1331
- Hultin, P.G.¹

4
- 29444451430
- W. Zou, Curr. Top. Med. Chem. 2005, 5, 1363-1391
- (2005) Curr. Top. Med. Chem. , vol.5 , pp. 1363-1391
- Zou, W.¹

5
- 0035171364
- P. Compain, O. R. Martin, Bioorg. Med. Chem. 2001, 9, 3077-3092
- (2001) Bioorg. Med. Chem. , vol.9 , pp. 3077-3092
- Compain, P.¹ Martin, O.R.²

6
- 0002212956
- F. Nicotra, Top. Curr. Chem. 1997, 187, 55-83.
- (1997) Top. Curr. Chem. , vol.187 , pp. 55-83
- Nicotra, F.¹

7
- 29244446754
- T. Bililign, B. R. Griffith, J. S. Thorson, Nat. Prod. Rep. 2005, 22, 742-760
- (2005) Nat. Prod. Rep. , vol.22 , pp. 742-760
- Bililign, T.¹ Griffith, B.R.² Thorson, J.S.³

8
- 33750477645
- K. W. Wellington, S. A. Benner, Nucleosides Nucleotides Nucleic Acids 2006, 25, 1309-1333.
- (2006) Nucleosides Nucleotides Nucleic Acids , vol.25 , pp. 1309-1333
- Wellington, K.W.¹ Benner, S.A.²

9
- 29444458427
- D. Y. W. Lee, M. He, Curr. Top. Med. Chem. 2005, 5, 1333-1350
- (2005) Curr. Top. Med. Chem. , vol.5 , pp. 1333-1350
- Lee, D.Y.W.¹ He, M.²

10
- 0034746037
- L. Somsák, Chem. Rev. 2001, 101, 81-135
- (2001) Chem. Rev. , vol.101 , pp. 81-135
- Somsák, L.¹

11
- 0032552046
- Y. Du, R. J. Linharrdt, Tetrahedron 1998, 54, 9913-9959
- (1998) Tetrahedron , vol.54 , pp. 9913-9959
- Du, Y.¹ Linharrdt, R.J.²

12
- 0028323434
- C. Jaramillo, S. Knapp, Synthesis 1994, 1-20
- (1994) Synthesis , pp. 1-20
- Jaramillo, C.¹ Knapp, S.²

13
- 0003522385
- (Tetrahedron Organic Chemistry Series, 13), Elsevier, Oxford
- D. E. Levy, C. Tang, in The Chemistry of C-glycosides (Tetrahedron Organic Chemistry Series, Vol. 13), Elsevier, Oxford, 1995
- (1995) The Chemistry of C-glycosides
- Levy, D.E.¹ Tang, C.²

14
- 0002476212
- J. M. Beau, T. Gallagher, Top. Curr. Chem. 1997, 187, 1-54
- (1997) Top. Curr. Chem. , vol.187 , pp. 1-54
- Beau, J.M.¹ Gallagher, T.²

15
- 79951953455
- M. Choumane, A. Banchet, N. Probst, S. Gérard, K. Plé, A. Haudrechy, C. R. Chim. 2011, 14, 235-273.
- (2011) C. R. Chim. , vol.14 , pp. 235-273
- Choumane, M.¹ Banchet, A.² Probst, N.³ Gérard, S.⁴ Plé, K.⁵ Haudrechy, A.⁶

16
- 78650897872
- J. Zheng, S. Vedachalam, S. Xiang, X. W. Liu, Org. Lett. 2011, 13, 42-45
- (2011) Org. Lett. , vol.13 , pp. 42-45
- Zheng, J.¹ Vedachalam, S.² Xiang, S.³ Liu, X.W.⁴

17
- 80053053646
- G. Li, D. C. Xiong, X. S. Ye, Synlett 2011, 2410-2414
- (2011) Synlett , pp. 2410-2414
- Li, G.¹ Xiong, D.C.² Ye, X.S.³

18
- 79955491297
- R. S. Andrews, J. J. Becker, M. R. Gagné, Angew. Chem. 2010, 122, 7432-7434
- (2010) Angew. Chem. , vol.122 , pp. 7432-7434
- Andrews, R.S.¹ Becker, J.J.² Gagné, M.R.³

19
- 77957332454
- Angew. Chem. Int. Ed. 2010, 49, 7274-7276
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 7274-7276

20
- 62749135024
- H. Gong, R. S. Andrews, J. L. Zuccarello, S. J. Lee, M. R. Gagné, Org. Lett. 2009, 11, 879-882
- (2009) Org. Lett. , vol.11 , pp. 879-882
- Gong, H.¹ Andrews, R.S.² Zuccarello, J.L.³ Lee, S.J.⁴ Gagné, M.R.⁵

21
- 33947604111
- K. P. Kaliappan, A. V. Subrahmanyam, Org. Lett. 2007, 9, 1121-1124
- (2007) Org. Lett. , vol.9 , pp. 1121-1124
- Kaliappan, K.P.¹ Subrahmanyam, A.V.²

22
- 0037223535
- S. F. Martin, Pure Appl. Chem. 2003, 75, 63-70.
- (2003) Pure Appl. Chem. , vol.75 , pp. 63-70
- Martin, S.F.¹

23
- 33847301925
- H. Gong, R. Sinisi, M. R. Gagné, J. Am. Chem. Soc. 2007, 129, 1908-1909.
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 1908-1909
- Gong, H.¹ Sinisi, R.² Gagné, M.R.³

24
- 51749116202
- H. Gong, M. R. Gagné, J. Am. Chem. Soc. 2008, 130, 12177-12183.
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 12177-12183
- Gong, H.¹ Gagné, M.R.²

25
- 84863383425
- S. Lemaire, I. N. Houpis, T. Xiao, J. Li, E. Digard, C. Gozlan, R. Liu, A. Gavryushin, C. Diène, Y. Wang, V. Farina, P. Knochel, Org. Lett. 2012, 14, 1480-1483.
- (2012) Org. Lett. , vol.14 , pp. 1480-1483
- Lemaire, S.¹ Houpis, I.N.² Xiao, T.³ Li, J.⁴ Digard, E.⁵ Gozlan, C.⁶ Liu, R.⁷ Gavryushin, A.⁸ Diène, C.⁹ Wang, Y.¹⁰ Farina, V.¹¹ Knochel, P.¹²

26
- 54849172400
- A. Guérinot, S. Reymond, J. Cossy, Angew. Chem. 2007, 119, 6641-6644
- (2007) Angew. Chem. , vol.119 , pp. 6641-6644
- Guérinot, A.¹ Reymond, S.² Cossy, J.³

27
- 34548299141
- Angew. Chem. Int. Ed. 2007, 46, 6521-6524.
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 6521-6524

28
- 68149115671
- For a review on cross-coupling reactions involving secondary alkyl halides, see:, A. Rudolph, M. Lautens, Angew. Chem. 2009, 121, 2694-2708
- (2009) Angew. Chem. , vol.121 , pp. 2694-2708
- Rudolph, A.¹ Lautens, M.²

29
- 70349782336
- Angew. Chem. Int. Ed. 2009, 48, 2656-2670.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2656-2670

30
- 84890999876
- (Ed.: B. Plietker), Wiley-VCH, Weinheim
- Iron Catalysis in Organic Chemistry (Ed.:, B. Plietker,), Wiley-VCH, Weinheim, 2008
- (2008) Iron Catalysis in Organic Chemistry

31
- 79952656192
- R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 111, 1417-1492
- (2011) Chem. Rev. , vol.111 , pp. 1417-1492
- Jana, R.¹ Pathak, T.P.² Sigman, M.S.³

32
- 77956498399
- E. Nakamura, N. Yoshikai, J. Org. Chem. 2010, 75, 6061-6067
- (2010) J. Org. Chem. , vol.75 , pp. 6061-6067
- Nakamura, E.¹ Yoshikai, N.²

33
- 77956013866
- B. Plietker, Synlett 2010, 2049-2058
- (2010) Synlett , pp. 2049-2058
- Plietker, B.¹

34
- 67649099463
- W. M. Czaplik, M. Mayer, J. Cvengros, A. J. von Wangelin, ChemSusChem 2009, 2, 396-417
- (2009) ChemSusChem , vol.2 , pp. 396-417
- Czaplik, W.M.¹ Mayer, M.² Cvengros, J.³ Von Wangelin, A.J.⁴

35
- 57549083398
- B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500-1511
- (2008) Acc. Chem. Res. , vol.41 , pp. 1500-1511
- Sherry, B.D.¹ Fürstner, A.²

36
- 54849171100
- S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 3363-3367
- (2008) Angew. Chem. , vol.120 , pp. 3363-3367
- Enthaler, S.¹ Junge, K.² Beller, M.³

37
- 50049109778
- Angew. Chem. Int. Ed. 2008, 47, 3317-3321
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3317-3321

38
- 11144323895
- C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254.
- (2004) Chem. Rev. , vol.104 , pp. 6217-6254
- Bolm, C.¹ Legros, J.² Le Paih, J.³ Zani, L.⁴

39
- 84857566958
- X. Lin, F. Zheng, F. L. Qing, Organometallics 2012, 31, 1578-1582
- (2012) Organometallics , vol.31 , pp. 1578-1582
- Lin, X.¹ Zheng, F.² Qing, F.L.³

40
- 84865443668
- T. Hatakeyama, Y. Okada, Y. Yoshimoto, M. Nakamura, Angew. Chem. 2011, 123, 11165-11168
- (2011) Angew. Chem. , vol.123 , pp. 11165-11168
- Hatakeyama, T.¹ Okada, Y.² Yoshimoto, Y.³ Nakamura, M.⁴

41
- 80855128794
- Angew. Chem. Int. Ed. 2011, 50, 10973-10976
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 10973-10976

42
- 25144465934
- R. B. Bedford, M. Betham, D. W. Bruce, A. A. Danopoulos, R. M. Frost, M. Hird, Chem. Commun. 2005, 4161-4163
- (2005) Chem. Commun. , pp. 4161-4163
- Bedford, R.B.¹ Betham, M.² Bruce, D.W.³ Danopoulos, A.A.⁴ Frost, R.M.⁵ Hird, M.⁶

43
- 10044237251
- R. Martin, A. Fürstner, Angew. Chem. 2004, 116, 4045-4047
- (2004) Angew. Chem. , vol.116 , pp. 4045-4047
- Martin, R.¹ Fürstner, A.²

44
- 4544294922
- Angew. Chem. Int. Ed. 2004, 43, 3955-3957
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3955-3957

45
- 0031973382
- Y. Hayashi, H. Shinokubo, K. Oshima, Tetrahedron Lett. 1998, 39, 63-66.
- (1998) Tetrahedron Lett. , vol.39 , pp. 63-66
- Hayashi, Y.¹ Shinokubo, H.² Oshima, K.³

46
- 0005335621
- N. Miquel, G. Doisneau, J. M. Beau, Angew. Chem. 2000, 112, 4277-4280
- (2000) Angew. Chem. , vol.112 , pp. 4277-4280
- Miquel, N.¹ Doisneau, G.² Beau, J.M.³

47
- 0034680596
- Angew. Chem. Int. Ed. 2000, 39, 4111-4114
- (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4111-4114

48
- 37049075549
- H. G. Korth, J. Dupuis, B. Giese, J. Chem. Soc. Perkin Trans. 2 1986, 1453-1459
- (1986) J. Chem. Soc. Perkin Trans. 2 , pp. 1453-1459
- Korth, H.G.¹ Dupuis, J.² Giese, B.³

49
- 0001326751
- J. Dupuis, B. Giese, J. Am. Chem. Soc. 1985, 107, 4332-4333
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 4332-4333
- Dupuis, J.¹ Giese, B.²

50
- 0342887443
- J. Dupuis, B. Giese, D. Rüegge, H. Fischer, H. G. Korth, R. Sustmann, Angew. Chem. 1984, 96, 887-888
- (1984) Angew. Chem. , vol.96 , pp. 887-888
- Dupuis, J.¹ Giese, B.² Rüegge, D.³ Fischer, H.⁴ Korth, H.G.⁵ Sustmann, R.⁶

51
- 84985520838
- Angew. Chem. Int. Ed. Engl. 1984, 23, 896-898
- (1984) Angew. Chem. Int. Ed. Engl. , vol.23 , pp. 896-898

52
- 0001081937
- B. Giese, J. Dupuis, Angew. Chem. 1983, 95, 633-634
- (1983) Angew. Chem. , vol.95 , pp. 633-634
- Giese, B.¹ Dupuis, J.²

53
- 84985534838
- Angew. Chem. Int. Ed. Engl. 1983, 22, 622-623
- (1983) Angew. Chem. Int. Ed. Engl. , vol.22 , pp. 622-623

54
- 37049094999
- R. M. Adlington, J. E. Baldwin, A. Basak, R. P. Kozyrod, J. Chem. Soc. Chem. Commun. 1983, 944-945.
- (1983) J. Chem. Soc. Chem. Commun. , pp. 944-945
- Adlington, R.M.¹ Baldwin, J.E.² Basak, A.³ Kozyrod, R.P.⁴

55
- 77949587544
- For a recent review, see:, G. Cahiez, A. Moyeux, Chem. Rev. 2010, 110, 1435-1462.
- (2010) Chem. Rev. , vol.110 , pp. 1435-1462
- Cahiez, G.¹ Moyeux, A.²

56
- 62149122121
- G. Cahiez, C. Chaboche, C. Duplais, A. Moyeux, Org. Lett. 2009, 11, 277-280
- (2009) Org. Lett. , vol.11 , pp. 277-280
- Cahiez, G.¹ Chaboche, C.² Duplais, C.³ Moyeux, A.⁴

57
- 63049124992
- M. Amatore, C. Gosmini, Chem. Commun. 2008, 5019-5021
- (2008) Chem. Commun. , pp. 5019-5021
- Amatore, M.¹ Gosmini, C.²

58
- 34247510669
- H. Someya, H. Ohmiya, H. Yorimitsu, K. Oshima, Org. Lett. 2007, 9, 1565-1567
- (2007) Org. Lett. , vol.9 , pp. 1565-1567
- Someya, H.¹ Ohmiya, H.² Yorimitsu, H.³ Oshima, K.⁴

59
- 34447539770
- H. Someya, H. Ohmiya, H. Yorimitsu, K. Oshima, Tetrahedron 2007, 63, 8609-8618
- (2007) Tetrahedron , vol.63 , pp. 8609-8618
- Someya, H.¹ Ohmiya, H.² Yorimitsu, H.³ Oshima, K.⁴

60
- 33746594544
- H. Ohmiya, H. Yorimitsu, K. Oshima, Org. Lett. 2006, 8, 3093-3096
- (2006) Org. Lett. , vol.8 , pp. 3093-3096
- Ohmiya, H.¹ Yorimitsu, H.² Oshima, K.³

61
- 33244462197
- H. Ohmiya, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2006, 128, 1886-1889
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 1886-1889
- Ohmiya, H.¹ Yorimitsu, H.² Oshima, K.³

62
- 32444451793
- H. Ohmiya, K. Wakabayashi, H. Yorimitsu, K. Oshima, Tetrahedron 2006, 62, 2207-2213
- (2006) Tetrahedron , vol.62 , pp. 2207-2213
- Ohmiya, H.¹ Wakabayashi, K.² Yorimitsu, H.³ Oshima, K.⁴

63
- 33644540458
- H. Yorimitsu, K. Oshima, Pure Appl. Chem. 2006, 78, 441-449
- (2006) Pure Appl. Chem. , vol.78 , pp. 441-449
- Yorimitsu, H.¹ Oshima, K.²

64
- 33751265316
- H. Someya, A. Kondoh, A. Sato, H. Ohmiya, H. Yorimitsu, K. Oshima, Synlett 2006, 3061-3062
- (2006) Synlett , pp. 3061-3062
- Someya, H.¹ Kondoh, A.² Sato, A.³ Ohmiya, H.⁴ Yorimitsu, H.⁵ Oshima, K.⁶

65
- 9244228468
- H. Ohmiya, T. Tsuji, H. Yorimitsu, K. Oshima, Chem. Eur. J. 2004, 10, 5640-5648
- (2004) Chem. Eur. J. , vol.10 , pp. 5640-5648
- Ohmiya, H.¹ Tsuji, T.² Yorimitsu, H.³ Oshima, K.⁴

66
- 9244251206
- T. Tsuji, H. Yorimitsu, K. Oshima, Angew. Chem. 2002, 114, 4311-4313
- (2002) Angew. Chem. , vol.114 , pp. 4311-4313
- Tsuji, T.¹ Yorimitsu, H.² Oshima, K.³

67
- 0037021014
- Angew. Chem. Int. Ed. 2002, 41, 4137-4139
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4137-4139

68
- 0034801334
- K. Wakabayashi, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2001, 123, 5374-5375.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 5374-5375
- Wakabayashi, K.¹ Yorimitsu, H.² Oshima, K.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.