Synthesis of 2-amino-2'-diphenylphosphino-1,1'-binaphthyl (MAP) and its accelerating effect on the Pd(0)-catalyzed N-arylation

Tetrahedron Letters

Volumn 39, Issue 50, 1998, Pages 9289-9292

  Vyskočil, Štěpán ^a,b   Smrčina, Martin ^a   Kočovský, Pavel ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 2' DIPHENYLPHOSPHINO 1,1' BINAPHTHYL; NAPHTHYL GROUP; PALLADIUM; UNCLASSIFIED DRUG;

ALKYLATION; ANALYTIC METHOD; ARTICLE; CATALYSIS; CELL TRANSFORMATION; CHIRALITY; DRUG SYNTHESIS; METHODOLOGY; NONHUMAN;

EID: 0032506564     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02088-7     Document Type: Article

References (38)

1. (1) (a) Paradisi, C. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991.
2. (b) Anderson, J. C.; Harding, M. Chem. Commun. 1998, 393 and refs. given therein.
3. (2) (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
4. (b) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268.
5. (c) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 720, 3694.
6. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. For reviews, see:
7. (e) Hartwig, J. F. Synlett 1997, 329.
8. (f) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046.
9. (3) (a) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
10. (b) Singer, R. A.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 720, 213.
11. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264.
12. (d) Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
13. (e) Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 779, 6054.
14. (4) (a) Smrčina, M.; Lorenc, M.; Hanuš, V.; Sedmera, P.; Kočovský, P. J. Org. Chem. 1992, 57, 1917.
15. (b) Smrčina, M.; Poláková, J.; Vyskočil, Š.; Kočovský, P. J. Org. Chem. 1993, 58, 4534.
16. (c) Smrčina, M.; Vyskočil, Š.; Polívková, J.; Poláková, J.; Kočovsky, P. Collect. Czech. Chem. Commun. 1996, 67, 1520.
17. (d) Smrčina, M.; Vyskočil, Š.; Hanuš, V.; Polášek, M.; Langer, V.; Zax, D. B.; Chew, B. G. M.; Verrier, H.; Harper, K.; Claxton, T. A.; Kočovský, P. J. Am. Chem. Soc. 1996, 118, 4878.
18. (e) Smrčina, M.; Vyskočil, Š.; Polívková, J.; Poláková, J.; Sejbal, J.; Hanuš, V.; Polášek, M.; Verrier, H.; Kočovský, P. Tetrahedron: Asymmetry 1997, 8, 537.
19. (f) Vyskočil, Š.; Smrčina, M.; Lorenc, M.; Hanuš, V.; Polášek, M.; Kočovský, P. Chem. Commun. 1998, 585.
20. (5) Abbott, A. P.; Cheung, C.; Kočovský, P. manuscript in preparation.
21. (6) (a) Carreira, E. M.; Singer, R. A.; Wheeseong, L. J. Am. Chem. Soc. 1994, 116, 8837.
22. (b) Carreira, E. M.; Wheeseong, L.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649.
23. (c) Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360.
24. (d) Knölker, H.-J.; Hermann, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 341.
25. (7) (a) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887.
26. (b) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 720, 1681. For a review, see:
27. (c) Hayashi, T. Acta Chem. Scand. 1996, 50, 259.
28. (8) Mahmoud, H.; Han, Y.; Segal, B. M.; Cai, L. Tetrahedron: Asymmetry 1998, 9, 2035.
29. (9) For the method, see ref 7 and: (a) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1994, 59, 7180.
30. (b) Kurz, L.; Lee, G.; Morgans, Jr., D.; Waldyke, M. J.; Wars, T. Tetrahedron Lett. 1990, 37, 6321.
31. 7,9 the coupling failed, leaving the starting triflate unreacted.
32. 2+; starting with (R)-1 of ≥99% ee, the resulting (R)-3 was of ≥97 % ee.
33. (12) This procedure was also carried out in the racemic series to obtain standards for determination of the enantiopurity.
34. 2NH required 80 °C for 5 h with the latter ligand.
35. 3.
36. (15) For the first attempts at kinetic resolution in the Hartwig-Buchwald coupling, see: Rossen, K.; Pye, P. J.; Maliakal, A.; Volante, R. P. J Org. Chem. 1997, 62, 6462.
37. 2d the reaction reached completion at 110 °C in 16 or 24 h (with diphosphine ligands).
38. 13