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European Journal of Organic Chemistry

Volumn 2014, Issue 20, 2014, Pages 4335-4341

Total synthesis of (±)-paroxetine by diastereoconvergent cobalt-catalysed arylation

(4) Despiau, Carole F a Dominey, Andrew P b Harrowven, David C a Linclau, Bruno a

a UNIVERSITY OF SOUTHAMPTON (United Kingdom)

b GLAXOSMITHKLINE (United Kingdom)

Author keywords

Cobalt; Cross coupling; Homogeneous catalysis; Nitrogen heterocycles; Radicals; Total synthesis

Indexed keywords

EID: 84903726895 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.201402108 Document Type: Article

Times cited : (23)

References (64)

1
- 79952656192
- R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 11, 1417-1492.
- (2011) Chem. Rev. , vol.11 , pp. 1417-1492
- Jana, R.¹ Pathak, T.P.² Sigman, M.S.³

2
- 77949587544
- G. Cahiez, A. Moyeux, Chem. Rev. 2010, 110, 1435-1462.
- (2010) Chem. Rev. , vol.110 , pp. 1435-1462
- Cahiez, G.¹ Moyeux, A.²

3
- 77956498399
- E. Nakamura, N. J. Yoshikai, Org. Chem. 2010, 75, 6061-6067.
- (2010) Org. Chem. , vol.75 , pp. 6061-6067
- Nakamura, E.¹ Yoshikai, N.J.²

4
- 70349782336
- Angew. Chem. 2009, 121, 2694 -2708
- A. Rudolph, M. Lautens, Angew. Chem. Int. Ed. 2009, 48, 2656-2670; Angew. Chem. 2009, 121, 2694 -2708.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2656-2670
- Rudolph, A.¹ Lautens, M.²

5
- 60149095698
- Angew. Chem. 2009, 121, 1390 -1393
- A. Fürstner, Angew. Chem. Int. Ed. 2009, 48, 1364-1367; Angew. Chem. 2009, 121, 1390 -1393.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1364-1367
- Fürstner, A.¹

6
- 67649099463
- W. M. Czaplik, M. Mayer, J. Cvengros, A. Jacobi von Wangelin, ChemSusChem 2009, 2, 396-417.
- (2009) ChemSusChem , vol.2 , pp. 396-417
- Czaplik, W.M.¹ Mayer, M.² Cvengros, J.³ Jacobi Von Wangelin, A.⁴

7
- 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

8
- 47249113368
- C. Gosmini, J.-M. Bégouin, A. Moncomble, Chem. Commun. 2008, 3221-3233.
- (2008) Chem. Commun. , pp. 3221-3233
- Gosmini, C.¹ Bégouin, J.-M.² Moncomble, A.³

9
- 77956013866
- B. Plietker, Synlett 2010, 2049-2058.
- (2010) Synlett , pp. 2049-2058
- Plietker, B.¹

10
- 1642361256
- M. Nakamura, K. Matsuo, S. Ito, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686-3687.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 3686-3687
- Nakamura, M.¹ Matsuo, K.² Ito, S.³ Nakamura, E.⁴

11
- 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

12
- 32144461712
- R. B. Bedford, M. Betham, D. W. Bruce, A. A. Danopoulos, R. M. Frost, M. Hird, J. Org. Chem. 2006, 71, 1104-1110.
- (2006) J. Org. Chem. , vol.71 , pp. 1104-1110
- Bedford, R.B.¹ Betham, M.² Bruce, D.W.³ Danopoulos, A.A.⁴ Frost, R.M.⁵ Hird, M.⁶

13
- 34547789922
- B. Saito, G. C. Fu, J. Am. Chem. Soc. 2007, 129, 9602-9603.
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 9602-9603
- Saito, B.¹ Fu, G.C.²

14
- 84865245127
- P. M. Perez Garcia, T. Di Franco, A. Orsino, P. Ren, X. Hu, Org. Lett. 2012, 14, 4286-4289.
- (2012) Org. Lett. , vol.14 , pp. 4286-4289
- Perez Garcia, P.M.¹ Di Franco, T.² Orsino, A.³ Ren, P.⁴ Hu, X.⁵

15
- 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

16
- 79955398877
- X. Yu, T. Yang, S. Wang, H. Xu, H. Gong, Org. Lett. 2011, 13, 2138-2141.
- (2011) Org. Lett. , vol.13 , pp. 2138-2141
- Yu, X.¹ Yang, T.² Wang, S.³ Xu, H.⁴ Gong, H.⁵

17
- 34447275675
- Angew. Chem. 2007, 119, 4442 -4444
- G. Cahiez, V. Habiak, C. Duplais, A. Moyeux, Angew. Chem. Int. Ed. 2007, 46, 4364-4366; Angew. Chem. 2007, 119, 4442 -4444.
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 4364-4366
- Cahiez, G.¹ Habiak, V.² Duplais, C.³ Moyeux, A.⁴

18
- 30444440562
- Angew. Chem. 2006, 118, 454 -458
- A. Fürstner, H. Krause, C. W. Lehmann, Angew. Chem. Int. Ed. 2006, 45, 440-444; Angew. Chem. 2006, 118, 454 -458.
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 440-444
- Fürstner, A.¹ Krause, H.² Lehmann, C.W.³

19
- 46949098763
- A. Fürstner, R. Martin, H. Krause, G. Seidel, R. Goddard, C. W. Lehmann, J. Am. Chem. Soc. 2008, 130, 8773-8787.
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 8773-8787
- Fürstner, A.¹ Martin, R.² Krause, H.³ Seidel, G.⁴ Goddard, R.⁵ Lehmann, C.W.⁶

20
- 0009214176
- R. B. Allen, R. G. Lawler, H. R. Ward, J. Am. Chem. Soc. 1973, 95, 1692-1693.
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 1692-1693
- Allen, R.B.¹ Lawler, R.G.² Ward, H.R.³

21
- 33847798672
- R. G. Lawler, P. Livant, J. Am. Chem. Soc. 1976, 98, 3710-3712.
- (1976) J. Am. Chem. Soc. , vol.98 , pp. 3710-3712
- Lawler, R.G.¹ Livant, P.²

22
- 0037021014
- Co-catalysed coupling involving trans-2-(1-octynyl)-3-iodotetrahydropyran gave an 86:14 trans/cis selectivity:, Angew. Chem. 2002, 114, 4311 -4313
- Co-catalysed coupling involving trans-2-(1-octynyl)-3-iodotetrahydropyran gave an 86:14 trans/cis selectivity:, T. Tsuji, H. Yorimitsu, K. Oshima, Angew. Chem. Int. Ed. 2002, 41, 4137-4139; Angew. Chem. 2002, 114, 4311 -4313.
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4137-4139
- Tsuji, T.¹ Yorimitsu, H.² Oshima, K.³

23
- 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

24
- 84875820709
- D. A. Devalankar, P. U. Karabal, A. Sudalai, Org. Biomol. Chem. 2013, 11, 1280-1285.
- (2013) Org. Biomol. Chem. , vol.11 , pp. 1280-1285
- Devalankar, D.A.¹ Karabal, P.U.² Sudalai, A.³

25
- 84867012843
- N. R. Chaubey, S. K. Ghosh, Tetrahedron: Asymmetry 2012, 23, 1206-1212.
- (2012) Tetrahedron: Asymmetry , vol.23 , pp. 1206-1212
- Chaubey, N.R.¹ Ghosh, S.K.²

26
- 84866732728
- Z.-T. He, Y.-B. Wei, H.-J. Yu, C.-Y. Sun, C.-G. Feng, P. Tian, G.-Q. Lin, Tetrahedron 2012, 68, 9186-9191.
- (2012) Tetrahedron , vol.68 , pp. 9186-9191
- He, Z.-T.¹ Wei, Y.-B.² Yu, H.-J.³ Sun, C.-Y.⁴ Feng, C.-G.⁵ Tian, P.⁶ Lin, G.-Q.⁷

27
- 80054006801
- S. Číhalová, G. Valero, J. Schimer, M. Humpl, M. Dračínský, A. Moyano, R. Rios, J. Vesely, Tetrahedron 2011, 67, 8942-8950.
- (2011) Tetrahedron , vol.67 , pp. 8942-8950
- Číhalová, S.¹ Valero, G.² Schimer, J.³ Humpl, M.⁴ Dračínský, M.⁵ Moyano, A.⁶ Rios, R.⁷ Vesely, J.⁸

28
- 79951810377
- S. Somaiah, S. Sashikanth, V. Raju, K. V. Reddy, Tetrahedron: Asymmetry 2011, 22, 1-3.
- (2011) Tetrahedron: Asymmetry , vol.22 , pp. 1-3
- Somaiah, S.¹ Sashikanth, S.² Raju, V.³ Reddy, K.V.⁴

29
- 77953558609
- M.-H. Kim, Y. Park, B.-S. Jeong, H.-G. Park, S.-S. Jew, Org. Lett. 2010, 12, 2826-2829.
- (2010) Org. Lett. , vol.12 , pp. 2826-2829
- Kim, M.-H.¹ Park, Y.² Jeong, B.-S.³ Park, H.-G.⁴ Jew, S.-S.⁵

30
- 61749096057
- G. Valero, J. Schimer, I. Cisarova, J. Vesely, A. Moyano, R. Rios, Tetrahedron Lett. 2009, 50, 1943-1946.
- (2009) Tetrahedron Lett. , vol.50 , pp. 1943-1946
- Valero, G.¹ Schimer, J.² Cisarova, I.³ Vesely, J.⁴ Moyano, A.⁵ Rios, R.⁶

31
- 45849102419
- P. S. Hynes, P. A. Stupple, D. J. Dixon, Org. Lett. 2008, 10, 1389-1391.
- (2008) Org. Lett. , vol.10 , pp. 1389-1391
- Hynes, P.S.¹ Stupple, P.A.² Dixon, D.J.³

32
- 41649092639
- A. Ma, S. Zhu, D. Ma, Tetrahedron Lett. 2008, 49, 3075-3077.
- (2008) Tetrahedron Lett. , vol.49 , pp. 3075-3077
- Ma, A.¹ Zhu, S.² Ma, D.³

33
- 38749093308
- Review
- Review:, C. De Risi, G. Fanton, G. P. Pollini, C. Trapella, F. Valente, V. Zanirato, Tetrahedron: Asymmetry 2008, 19, 131-155.
- (2008) Tetrahedron: Asymmetry , vol.19 , pp. 131-155
- De Risi, C.¹ Fanton, G.² Pollini, G.P.³ Trapella, C.⁴ Valente, F.⁵ Zanirato, V.⁶

34
- 0031984009
- N. S. Gunasekara, S. Noble, P. Benfield, Drugs 1998, 55, 85-120.
- (1998) Drugs , vol.55 , pp. 85-120
- Gunasekara, N.S.¹ Noble, S.² Benfield, P.³

35
- 0036207307
- A. J. Wagstaff, S. M. Cheer, A. J. Matheson, D. Ormrod, K. L. Goa, Drugs 2002, 62, 655-703.
- (2002) Drugs , vol.62 , pp. 655-703
- Wagstaff, A.J.¹ Cheer, S.M.² Matheson, A.J.³ Ormrod, D.⁴ Goa, K.L.⁵

36
- 33644770072
- K. Bica, P. Gaertner, Org. Lett. 2006, 8, 733-735.
- (2006) Org. Lett. , vol.8 , pp. 733-735
- Bica, K.¹ Gaertner, P.²

37
- 22244440830
- M. Nakamura, S. Ito, K. Matsuo, E. Nakamura, Synlett 2005, 1794-1798.
- (2005) Synlett , pp. 1794-1798
- Nakamura, M.¹ Ito, S.² Matsuo, K.³ Nakamura, E.⁴

38
- 34548299141
- Angew. Chem. 2007, 119, 6641 -6644
- A. Guérinot, S. Reymond, J. Cossy, Angew. Chem. Int. Ed. 2007, 46, 6521-6524; Angew. Chem. 2007, 119, 6641 -6644.
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 6521-6524
- Guérinot, A.¹ Reymond, S.² Cossy, J.³

39
- 70349913902
- T. Hatakeyama, N. Nakagawa, M. Nakamura, Org. Lett. 2009, 11, 4496-4499.
- (2009) Org. Lett. , vol.11 , pp. 4496-4499
- Hatakeyama, T.¹ Nakagawa, N.² Nakamura, M.³

40
- 80855128794
- Angew. Chem. 2011, 123, 11165 -11168
- T. Hatakeyama, Y. Okada, Y. Yoshimoto, M. Nakamura, Angew. Chem. Int. Ed. 2011, 50, 10973-10976; Angew. Chem. 2011, 123, 11165 -11168.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 10973-10976
- Hatakeyama, T.¹ Okada, Y.² Yoshimoto, Y.³ Nakamura, M.⁴

41
- 84856093673
- T. Hashimoto, T. Hatakeyama, M. Nakamura, J. Org. Chem. 2012, 77, 1168-1173.
- (2012) J. Org. Chem. , vol.77 , pp. 1168-1173
- Hashimoto, T.¹ Hatakeyama, T.² Nakamura, M.³

42
- 84865430683
- K. K. A. D. S. Kathriarachchi, Angew. Chem. 2012, 124, 8964 -8967
- T. Hatakeyama, T. Hashimoto, K. K. A. D. S. Kathriarachchi, T. Zenmyo, H. Seike, M. Nakamura, Angew. Chem. Int. Ed. 2012, 51, 8834-8837; Angew. Chem. 2012, 124, 8964 -8967.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 8834-8837
- Hatakeyama, T.¹ Hashimoto, T.² Zenmyo, T.³ Seike, H.⁴ Nakamura, M.⁵

43
- 84876540773
- M. Guisan-Ceinos, F. Tato, E. Bunuel, P. Calle, D. J. Cardenas, Chem. Sci. 2013, 4, 1098-1104.
- (2013) Chem. Sci. , vol.4 , pp. 1098-1104
- Guisan-Ceinos, M.¹ Tato, F.² Bunuel, E.³ Calle, P.⁴ Cardenas, D.J.⁵

44
- 77956500677
- Angew. Chem. 2010, 122, 6826-6828 (Ni, >95:5)
- Z. Lu, G. C. Fu, Angew. Chem. Int. Ed. 2010, 49, 6676-6678; Angew. Chem. 2010, 122, 6826-6828 (Ni, >95:5)
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 6676-6678
- Lu, Z.¹ Fu, G.C.²

45
- 79953020974
- Angew. Chem. 2011, 123, 3361-3365 (Fe, >95:5)
- A. K. Steib, T. Thaler, K. Komeyana, P. Mayer, P. Knochel, Angew. Chem. Int. Ed. 2011, 50, 3303-3307; Angew. Chem. 2011, 123, 3361-3365 (Fe, >95:5).
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 3303-3307
- Steib, A.K.¹ Thaler, T.² Komeyana, K.³ Mayer, P.⁴ Knochel, P.⁵

46
- 21044444206
- J. Cossy, Chem. Rec. 2005, 5, 70-80.
- (2005) Chem. Rec. , vol.5 , pp. 70-80
- Cossy, J.¹

47
- 0033775563
- D. O'Hagan, Nat. Prod. Rep. 2000, 17, 435-446.
- (2000) Nat. Prod. Rep. , vol.17 , pp. 435-446
- O'Hagan, D.¹

48
- 84873481979
- A. Cochi, D. Gomez Pardo, J. Cossy, Eur. J. Org. Chem. 2013, 809-829.
- (2013) Eur. J. Org. Chem. , pp. 809-829
- Cochi, A.¹ Gomez Pardo, D.² Cossy, J.³

49
- 77952158798
- F. P. J. T. Rutjes
- M. A. Wijdeven, J. Willemsen, F. P. J. T. Rutjes, Eur. J. Org. Chem. 2010, 2831-2844.
- (2010) Eur. J. Org. Chem. , pp. 2831-2844
- Wijdeven, M.A.¹ Willemsen, J.²

50
- 38549126119
- S. Källström, R. Leino, Bioorg. Med. Chem. 2008, 16, 601-635.
- (2008) Bioorg. Med. Chem. , vol.16 , pp. 601-635
- Källström, S.¹ Leino, R.²

51
- 0842268019
- M. G. P. Buffat
- M. G. P. Buffat, Tetrahedron 2004, 60, 1701-1729.
- (2004) Tetrahedron , vol.60 , pp. 1701-1729

52
- 0037459890
- P. M. Weintraub, J. S. Sabol, J. M. Kane, D. R. Borcherding, Tetrahedron 2003, 59, 2953-2989.
- (2003) Tetrahedron , vol.59 , pp. 2953-2989
- Weintraub, P.M.¹ Sabol, J.S.² Kane, J.M.³ Borcherding, D.R.⁴

53
- 0141925985
- F.-X. Felpin, J. Lebreton, Eur. J. Org. Chem. 2003, 3693-3712.
- (2003) Eur. J. Org. Chem. , pp. 3693-3712
- Felpin, F.-X.¹ Lebreton, J.²

54
- 0033709712
- S. Laschat, T. Dickner, Synthesis 2000, 1781-1813.
- (2000) Synthesis , pp. 1781-1813
- Laschat, S.¹ Dickner, T.²

55
- 0025615325
- J. Lázár, G. Bernáth, J. Heterocycl. Chem. 1990, 27, 1885-1892.
- (1990) J. Heterocycl. Chem. , vol.27 , pp. 1885-1892
- Lázár, J.¹ Bernáth, G.²

56
- 13944261905
- P. C. Ting, J. F. Lee, J. Wu, S. P. Umland, R. Aslanian, J. Cao, Y. Dong, C. G. Garlisi, E. J. Gilbert, Y. Huang, J. Jakway, J. Kelly, Z. Liu, S. McCombie, H. Shah, F. Tian, Y. Wan, N.-Y. Shih, Bioorg. Med. Chem. Lett. 2005, 15, 1375-1378.
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 1375-1378
- Ting, P.C.¹ Lee, J.F.² Wu, J.³ Umland, S.P.⁴ Aslanian, R.⁵ Cao, J.⁶ Dong, Y.⁷ Garlisi, C.G.⁸ Gilbert, E.J.⁹ Huang, Y.¹⁰ Jakway, J.¹¹ Kelly, J.¹² Liu, Z.¹³ McCombie, S.¹⁴ Shah, H.¹⁵ Tian, F.¹⁶ Wan, Y.¹⁷ Shih, N.-Y.¹⁸

57
- 85083233801
- K. Soai, H. Oyamada, Synthesis 1984, 605-607.
- (1984) Synthesis , pp. 605-607
- Soai, K.¹ Oyamada, H.²

58
- 2442655977
- T. Nagano, T. Hayashi, Org. Lett. 2004, 6, 1297-1299.
- (2004) Org. Lett. , vol.6 , pp. 1297-1299
- Nagano, T.¹ Hayashi, T.²

59
- 84856485748
- Angew. Chem. 2012, 124, 1386 -1390
- S. Guelak, A. Jacobi von Wangelin, Angew. Chem. Int. Ed. 2012, 51, 1357-1361; Angew. Chem. 2012, 124, 1386 -1390.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1357-1361
- Guelak, S.¹ Jacobi Von Wangelin, A.²

60
- 0037146041
- A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856-13863.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 13856-13863
- Fürstner, A.¹ Leitner, A.² Méndez, M.³ Krause, H.⁴

61
- 0037083916
- Angew. Chem. 2002, 114, 632 -635
- A. Fürstner, A. Leitner, Angew. Chem. Int. Ed. 2002, 41, 609-612; Angew. Chem. 2002, 114, 632 -635.
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 609-612
- Fürstner, A.¹ Leitner, A.²

62
- 84867824929
- L. Nicolas, P. Angibaud, I. Stansfield, P. Bonnet, L. Meerpoel, S. Reymond, J. Cossy, Angew. Chem. Int. Ed. 2012, 51, 11101-11104.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 11101-11104
- Nicolas, L.¹ Angibaud, P.² Stansfield, I.³ Bonnet, P.⁴ Meerpoel, L.⁵ Reymond, S.⁶ Cossy, J.⁷

63
- 0141725892
- M. S. Taylor, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 11204-11205.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 11204-11205
- Taylor, M.S.¹ Jacobsen, E.N.²

64
- 33846907785
- J. F. Bower, T. Riis-Johannessen, P. Szeto, A. J. Whitehead, T. Gallagher, Chem. Commun. 2007, 728-730.
- (2007) Chem. Commun. , pp. 728-730
- Bower, J.F.¹ Riis-Johannessen, T.² Szeto, P.³ Whitehead, A.J.⁴ Gallagher, T.⁵

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