N-Arylation of α-aminoesters with p-tolylboronic acid promoted by copper(II) acetate

Tetrahedron Letters

Volumn 44, Issue 8, 2003, Pages 1691-1694

  Lam, Patrick Y S ^a   Bonne, Damien ^a   Vincent, Guillaume ^a   Clark, Charles G ^a   Combs, Andrew P ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 TOLYLBORONIC ACID; BORONIC ACID DERIVATIVE; COPPER; COPPER ACETATE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; RACEMIC MIXTURE; ROOM TEMPERATURE;

EID: 0037450499     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02882-4     Document Type: Article

References (35)

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11. For solid-phase N-arylation, see: (a) Combs, A. P.; Tadesse, S.; Rafalski, M.; Haque, T. S.; Lam, P. Y. S. J. Comb. Chem. 2002, 4, 179-182; (b) Combs, A. P.; Rafalski, M. J. Comb. Chem. 2000, 2, 29-32; © Combs, A. P.; Saubern, S.; Rafalski, M.; Lam, P. Y. S. Tetrahedron Lett. 1999, 40, 1623-1626.
12. For solid-phase N-arylation, see: (a) Combs, A. P.; Tadesse, S.; Rafalski, M.; Haque, T. S.; Lam, P. Y. S. J. Comb. Chem. 2002, 4, 179-182; (b) Combs, A. P.; Rafalski, M. J. Comb. Chem. 2000, 2, 29-32; © Combs, A. P.; Saubern, S.; Rafalski, M.; Lam, P. Y. S. Tetrahedron Lett. 1999, 40, 1623-1626.
13. For solid-phase N-arylation, see: (a) Combs, A. P.; Tadesse, S.; Rafalski, M.; Haque, T. S.; Lam, P. Y. S. J. Comb. Chem. 2002, 4, 179-182; (b) Combs, A. P.; Rafalski, M. J. Comb. Chem. 2000, 2, 29-32; © Combs, A. P.; Saubern, S.; Rafalski, M.; Lam, P. Y. S. Tetrahedron Lett. 1999, 40, 1623-1626.
14. For S-arylation, see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312; (b) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022. For O-arylation, see: © Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hinterman, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (d) Simon, J.; Salzbrunn, S.; Surya Prakash, G. K.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (g) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. For N-arylation, see: (h) Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron Lett. 2000, 41, 9053-9057; (i) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (j) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
15. For S-arylation, see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312; (b) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022. For O-arylation, see: © Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hinterman, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (d) Simon, J.; Salzbrunn, S.; Surya Prakash, G. K.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (g) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. For N-arylation, see: (h) Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron Lett. 2000, 41, 9053-9057; (i) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (j) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
16. For S-arylation, see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312; (b) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022. For O-arylation, see: © Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hinterman, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (d) Simon, J.; Salzbrunn, S.; Surya Prakash, G. K.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (g) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. For N-arylation, see: (h) Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron Lett. 2000, 41, 9053-9057; (i) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (j) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
17. For S-arylation, see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312; (b) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022. For O-arylation, see: © Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hinterman, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (d) Simon, J.; Salzbrunn, S.; Surya Prakash, G. K.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (g) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. For N-arylation, see: (h) Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron Lett. 2000, 41, 9053-9057; (i) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (j) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
18. For S-arylation, see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312; (b) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022. For O-arylation, see: © Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hinterman, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (d) Simon, J.; Salzbrunn, S.; Surya Prakash, G. K.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (g) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. For N-arylation, see: (h) Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron Lett. 2000, 41, 9053-9057; (i) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (j) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
19. For S-arylation, see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312; (b) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022. For O-arylation, see: © Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hinterman, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (d) Simon, J.; Salzbrunn, S.; Surya Prakash, G. K.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (g) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. For N-arylation, see: (h) Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron Lett. 2000, 41, 9053-9057; (i) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (j) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
20. For S-arylation, see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312; (b) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022. For O-arylation, see: © Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hinterman, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (d) Simon, J.; Salzbrunn, S.; Surya Prakash, G. K.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (g) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. For N-arylation, see: (h) Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron Lett. 2000, 41, 9053-9057; (i) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (j) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
21. For S-arylation, see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312; (b) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022. For O-arylation, see: © Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hinterman, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (d) Simon, J.; Salzbrunn, S.; Surya Prakash, G. K.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (g) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. For N-arylation, see: (h) Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron Lett. 2000, 41, 9053-9057; (i) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (j) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
22. For S-arylation, see: (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309-4312; (b) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019-2022. For O-arylation, see: © Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hinterman, T. J. Am. Chem. Soc. 2001, 123, 12411-12413; (d) Simon, J.; Salzbrunn, S.; Surya Prakash, G. K.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2001, 66, 633-634; (e) Decicco, C. P.; Song, Y.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032; (f) Petrassi, H. M.; Sharpless, K. B.; Kelly, J. W. Org. Lett. 2001, 3, 139-142; (g) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977. For N-arylation, see: (h) Collot, V.; Bovy, P. R.; Rault, S. Tetrahedron Lett. 2000, 41, 9053-9057; (i) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770; (j) Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982.
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33. Chiral reverse-phase HPLC provided baseline resolution of the enantiomers from which any racemization could be determined.
34. The lack of racemization is in agreement with the findings of Combs and Rafalski (Ref. 4b) for arylation of sulfonamides.
35. 2 as the first step of the reaction.