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Chemical Communications

Volumn 47, Issue 38, 2011, Pages 10611-10613

Synthesis of 2,4,6-trisubstituted pyridines via an olefin cross-metathesis/Heck-cyclisation-elimination sequence

(6) Donohoe, Timothy J a Bower, John F a Baker, David B a Basutto, José A a Chan, Louis K M a Gallagher, Peter b

a UNIVERSITY OF OXFORD (United Kingdom)

b ELI LILLY AND COMPANY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS METATHESIS; CYCLIZATION; ELIMINATION REACTION; HECK REACTION; ONE POT SYNTHESIS;

EID: 80052947788 PISSN: 13597345 EISSN: 1364548X Source Type: Journal
DOI: 10.1039/c1cc14257g Document Type: Article

Times cited : (36)

References (41)

1
- 33645687253
- ed., Prentice Hall Europe, London
- Pharmaceutical Chemistry. Drug Synthesis, ed., H. J. Roth, and, A. Kleemann, Prentice Hall Europe, London, vol. 1, 1988, p. 407
- (1988) Pharmaceutical Chemistry. Drug Synthesis , vol.1 , pp. 407
- Roth, H.J.¹ Kleemann, A.²

2
- 0036270264
- For representative reviews
- V. Bonnet F. Mongin F. Trécourt G. Breton F. Marsais P. Knochel G. Queguiner Synlett 2002 1008
- (2002) Synlett , pp. 1008
- Bonnet, V.¹ Mongin, F.² Trécourt, F.³ Breton, G.⁴ Marsais, F.⁵ Knochel, P.⁶ Queguiner, G.⁷

3
- 33846223940
- G. Chelucci Chem. Soc. Rev. 2006 35 1230
- (2006) Chem. Soc. Rev. , vol.35 , pp. 1230
- Chelucci, G.¹

4
- 77954950120
- C. G. Arena G. Arico Curr. Org. Chem. 2010 14 546
- (2010) Curr. Org. Chem. , vol.14 , pp. 546
- Arena, C.G.¹ Arico, G.²

5
- 0033303396
- For reviews of pyridine synthesis
- A. von Zelewsky Coord. Chem. Rev. 1999 190 811
- (1999) Coord. Chem. Rev. , vol.190 , pp. 811
- Von Zelewsky, A.¹

6
- 3042558198
- G. D. Henry Tetrahedron 2004 60 6043
- (2004) Tetrahedron , vol.60 , pp. 6043
- Henry, G.D.¹

7
- 78249271716
- For a representative de novo method
- M. Hill Chem.-Eur. J. 2010 16 12052
- (2010) Chem.-Eur. J. , vol.16 , pp. 12052
- Hill, M.¹

8
- 18744382742
- For ring closing metathesis based syntheses of heteroaromatic compounds
- O. G. Dediu N. A. M. Yehia T. Oeser K. Polborn T. J. J. Müller Eur. J. Org. Chem. 2005 1834
- (2005) Eur. J. Org. Chem. , pp. 1834
- Dediu, O.G.¹ Yehia, N.A.M.² Oeser, T.³ Polborn, K.⁴ Müller, T.J.J.⁵

9
- 70349324513
- T. J. Donohoe J. F. Bower J. A. Basutto L. P. Fishlock P. A. Procopiou C. K. A. Callens Tetrahedron 2009 65 8969
- (2009) Tetrahedron , vol.65 , pp. 8969
- Donohoe, T.J.¹ Bower, J.F.² Basutto, J.A.³ Fishlock, L.P.⁴ Procopiou, P.A.⁵ Callens, C.K.A.⁶

10
- 65949112493
- T. J. Donohoe L. P. Fishlock J. A. Basutto J. F. Bower P. A. Procopiou A. L. Thompson Chem. Commun. 2009 3008
- (2009) Chem. Commun. , pp. 3008
- Donohoe, T.J.¹ Fishlock, L.P.² Basutto, J.A.³ Bower, J.F.⁴ Procopiou, P.A.⁵ Thompson, A.L.⁶

11
- 60849126719
- K. Yoshida F. Kawagoe K. Hayashi S. Horiuchi T. Imamoto A. Yanagisawa Org. Lett. 2009 11 515
- (2009) Org. Lett. , vol.11 , pp. 515
- Yoshida, K.¹ Kawagoe, F.² Hayashi, K.³ Horiuchi, S.⁴ Imamoto, T.⁵ Yanagisawa, A.⁶

12
- 37149024266
- T. J. Donohoe N. M. Kershaw A. J. Orr K. M. P. Wheelhouse (nee Gosby) L. P. Fishlock A. R. Lacy M. Bingham P. A. Procopiou Tetrahedron 2008 64 809
- (2008) Tetrahedron , vol.64 , pp. 809
- Donohoe, T.J.¹ Kershaw, N.M.² Orr, A.J.³ Wheelhouse, K.M.P.⁴ Fishlock, L.P.⁵ Lacy, A.R.⁶ Bingham, M.⁷ Procopiou, P.A.⁸

13
- 38749083069
- T. J. Donohoe L. P. Fishlock P. A. Procopiou Org. Lett. 2008 10 285
- (2008) Org. Lett. , vol.10 , pp. 285
- Donohoe, T.J.¹ Fishlock, L.P.² Procopiou, P.A.³

14
- 0000498386
- For a review
- O. Fujimura G. C. Fu R. H. Grubbs J. Org. Chem. 1994 59 4029
- (1994) J. Org. Chem. , vol.59 , pp. 4029
- Fujimura, O.¹ Fu, G.C.² Grubbs, R.H.³

15
- 68949096781
- For a recent report
- W. A. L. van Otterlo C. B. de Koning Chem. Rev. 2009 109 3743
- (2009) Chem. Rev. , vol.109 , pp. 3743
- Van Otterlo, W.A.L.¹ De Koning, C.B.²

16
- 79955604204
- references therein For recent representative examples
- M. Jaric B. A. Haag S. M. Manolikakes P. Knochel Org. Lett. 2011 13 2306
- (2011) Org. Lett. , vol.13 , pp. 2306
- Jaric, M.¹ Haag, B.A.² Manolikakes, S.M.³ Knochel, P.⁴

17
- 79955684836
- M. C. Ye G. L. Gao J. Q. Yu J. Am. Chem. Soc. 2011 133 6964
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 6964
- Ye, M.C.¹ Gao, G.L.² Yu, J.Q.³

18
- 77749280662
- R. E. Beveridge B. A. Arndtsen Synthesis 2010 1000
- (2010) Synthesis , pp. 1000
- Beveridge, R.E.¹ Arndtsen, B.A.²

19
- 76249098976
- J. J. Mousseau J. A. Bull A. B. Charette Angew. Chem., Int. Ed. 2010 49 1115
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 1115
- Mousseau, J.J.¹ Bull, J.A.² Charette, A.B.³

20
- 78650299781
- H.-Y. Sun S. I. Gorelsky D. R. Stuart L.-C. Campeau K. Fagnou J. Org. Chem. 2010 75 8180
- (2010) J. Org. Chem. , vol.75 , pp. 8180
- Sun, H.-Y.¹ Gorelsky, S.I.² Stuart, D.R.³ Campeau, L.-C.⁴ Fagnou, K.⁵

21
- 57349094283
- A. M. Berman J. C. Lewis R. G. Bergman J. A. Ellman J. Am. Chem. Soc. 2008 130 14926
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 14926
- Berman, A.M.¹ Lewis, J.C.² Bergman, R.G.³ Ellman, J.A.⁴

22
- 39749196066
- Y. Nakao K. S. Kanyiva T. Hiyama J. Am. Chem. Soc. 2008 130 2448
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 2448
- Nakao, Y.¹ Kanyiva, K.S.² Hiyama, T.³

23
- 77957304266
- Y. Nakao Y. Yamada N. Kashihara T. Hiyama J. Am. Chem. Soc. 2010 132 13666
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 13666
- Nakao, Y.¹ Yamada, Y.² Kashihara, N.³ Hiyama, T.⁴

24
- 77649252160
- T. J. Donohoe J. F. Bower Proc. Natl. Acad. Sci. U. S. A. 2010 107 3373
- (2010) Proc. Natl. Acad. Sci. U. S. A. , vol.107 , pp. 3373
- Donohoe, T.J.¹ Bower, J.F.²

25
- 77956604319
- T. J. Donohoe N. J. Race J. F. Bower C. K. A. Callens Org. Lett. 2010 12 4094
- (2010) Org. Lett. , vol.12 , pp. 4094
- Donohoe, T.J.¹ Race, N.J.² Bower, J.F.³ Callens, C.K.A.⁴

26
- 78649980508
- T. J. Donohoe J. F. Bower J. A. Basutto Nat. Protoc. 2010 5 2005
- (2010) Nat. Protoc. , vol.5 , pp. 2005
- Donohoe, T.J.¹ Bower, J.F.² Basutto, J.A.³

27
- 79952137170
- Geometric inversion of the alkene during the Heck reaction has previously been reported
- T. J. Donohoe J. A. Basutto J. F. Bower A. Rathi Org. Lett. 2011 13 1036
- (2011) Org. Lett. , vol.13 , pp. 1036
- Donohoe, T.J.¹ Basutto, J.A.² Bower, J.F.³ Rathi, A.⁴

28
- 0034838172
- NOE experiments from our previous work also proved that inversion occurs under the Heck reaction to allow cyclisation to form furans: see ref. 8a
- A. F. Littke G. C. Fu J. Am. Chem. Soc. 2001 123 6989
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 6989
- Littke, A.F.¹ Fu, G.C.²

29
- 0027936015
- L. Alcaraz J. J. Hamett C. Mioskowski J. P. Madel T. Le Gall D.-S. Shin J. R. Falck Tetrahedron Lett. 1994 35 5449
- (1994) Tetrahedron Lett. , vol.35 , pp. 5449
- Alcaraz, L.¹ Hamett, J.J.² Mioskowski, C.³ Madel, J.P.⁴ Le Gall, T.⁵ Shin, D.-S.⁶ Falck, J.R.⁷

30
- 33748667189
- Angew. Chem., Int. Ed. 2006 45 5510
- A. Füstner M. D. B. Fenster B. Fasching C. Godbout K. Radkowski Angew. Chem. 2006 118 5636 Angew. Chem., Int. Ed. 2006 45 5510
- (2006) Angew. Chem. , vol.118 , pp. 5636
- Füstner, A.¹ Fenster, M.D.B.² Fasching, B.³ Godbout, C.⁴ Radkowski, K.⁵

31
- 0043194171
- A. K. Chatterjee T.-L. Choi D. P. Sanders R. H. Grubbs J. Am. Chem. Soc. 2003 125 11360
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 11360
- Chatterjee, A.K.¹ Choi, T.-L.² Sanders, D.P.³ Grubbs, R.H.⁴

32
- 57549117034
- Intermediates associated with the synthesis of 4a (5a and 6a) were isolated. See ESI for full characterisation details Examples found upon a literature survey
- G. C. Fu Acc. Chem. Res. 2008 41 1555
- (2008) Acc. Chem. Res. , vol.41 , pp. 1555
- Fu, G.C.¹

33
- 79954506539
- L. Liao R. Jana K. B. Urkalan M. S. Sigman J. Am. Chem. Soc. 2011 133 5784
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 5784
- Liao, L.¹ Jana, R.² Urkalan, K.B.³ Sigman, M.S.⁴

34
- 84958133964
- Z. Owczarczyk F. Lamaty E. Vawter E. Negishi J. Am. Chem. Soc. 1992 114 10091
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 10091
- Owczarczyk, Z.¹ Lamaty, F.² Vawter, E.³ Negishi, E.⁴

35
- 0005047136
- L. Harris K. Jarowicki P. Kocienski R. Bell Synlett 1996 903
- (1996) Synlett , pp. 903
- Harris, L.¹ Jarowicki, K.² Kocienski, P.³ Bell, R.⁴

36
- 30944460157
- See ESI for results with lower catalyst/vinyl ketone loadings The structure of pyridine 4l was confirmed by characteristic NOE enhancements. See ESI for full details Despite an efficient cross metathesis (step 1), our efforts to persuade other substrates to undergo a one pot Heck (step 2) and cyclisation (step 3) resulted either in low conversion or decomposition. Ongoing work to widen the scope will be reported in due course
- T. Frenzel M. Brünjes M. Quitschalle A. Kirschning Org. Lett. 2006 8 135
- (2006) Org. Lett. , vol.8 , pp. 135
- Frenzel, T.¹ Brünjes, M.² Quitschalle, M.³ Kirschning, A.⁴

37
- 84983681648
- J. Cosier A. M. Glazer J. Appl. Crystallogr. 1986 19 105
- (1986) J. Appl. Crystallogr. , vol.19 , pp. 105
- Cosier, J.¹ Glazer, A.M.²

38
- 0031059866
- Z. Otwinowski and W. Minor, ed. C. W. Carter and R. M. Sweet, Methods Enzymol., Academic Press
- Z. Otwinowski and W. Minor, Processing of X-ray diffraction data collected in oscillation mode, ed. C. W. Carter and R. M. Sweet, Methods Enzymol., 1997, 276, Academic Press
- (1997) Processing of X-ray diffraction data collected in oscillation mode , vol.276

39
- 34447525419
- L. Palatinus G. Chapuis J. Appl. Crystallogr. 1997 40 786
- (1997) J. Appl. Crystallogr. , vol.40 , pp. 786
- Palatinus, L.¹ Chapuis, G.²

40
- 1242313195
- P. W. Betteridge J. R. Carruthers R. I. Cooper K. Prout D. J. Watkin J. Appl. Crystallogr. 2003 36 1487
- (2003) J. Appl. Crystallogr. , vol.36 , pp. 1487
- Betteridge, P.W.¹ Carruthers, J.R.² Cooper, R.I.³ Prout, K.⁴ Watkin, D.J.⁵

41
- 77956464770
- R. I. Cooper A. L. Thompson D. J. Watkin J. Appl. Crystallogr. 2010 43 1100
- (2010) J. Appl. Crystallogr. , vol.43 , pp. 1100
- Cooper, R.I.¹ Thompson, A.L.² Watkin, D.J.³

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