Palladium-catalyzed coupling of optically active amines with aryl bromides

Journal of the American Chemical Society

Volumn 119, Issue 36, 1997, Pages 8451-8458

  Wagaw, Seble ^a   Rennels, Roger A ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030760535     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971583o     Document Type: Article

References (39)

1. Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927-928.
2. Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901-7902.
3. Guram, A. S.; Rennels, R. R.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
4. Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969-5970.
5. Louie, J.; Hartwig, J. F. Tetrahedron Lett 1995, 36, 3609-3612.
6. Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240-7241.
7. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216.
8. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
9. Marcoux, J. F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568-1569.
10. Gupton, J. T.; Tarrant, J. G.; Yu, R. H.; Solarz, T. L. Synth. Comm. 1992, 22, 3205-3214.
11. Grundfeld, N.; Stanton, J. L.; Yuan, A. M.; Ebetino, F. H.; Browne, L. J.; Gude, C.; Huebner, C. F. J. Med. Chem. 1983, 26, 1277-1293.
12. LaMontagne, M. P.; Blumbergs, p.; Smith, D. C. J. Med. Chem. 1989, 32, 1728-1732.
13. Wender, P. A.; Zercher, C. K. J. Am. Chem. Soc. 1991, 113, 2311-2313.
14. Carmeli, S.; Moore, R. E.; Patterson, G. M. L. J. Am. Chem. Soc. 1990, 112, 8195-8197.
15. Queener, S. F.; Bartlett, M. S.; Nasar, M.; Smith, J. W. Antimicrob. Agents Chemother. 1993, 37, 2166-2172.
16. Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997-8.
17. For previous exmaples of palladium-catalyzed intramolecular aryl aminations and aryl amidations, see: Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525-7546.
18. Harrington, P. J.; Hegedus, L. S.; McDaniel, K. F. J. Am. Chem. Soc. 1987, 109, 4335-4338.
19. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.
20. Tombo, G. M. R.; Schär, H. P.; Ghisalba, O. Agric. Biol. Chem. 1987, 51, 1833-1838.
21. The use of less expensive bis(phosphine) ligands, such as 1,2-bis-(diphenylphosphino)ethane, l,3-bis(diphenylphosphino)propane, and 1,2-bis(diphenylphosphino)benzene, also prevents racemization in these reactions. However, the yields of coupled products are significantly lower due to poor conversion and an increase of side products which arise from β-hydride elimination from Pd(II)-amido complexes. See ref 7.
22. Overman has recently used our methodology to aid in the determination of the absolute configuration of an amino alcohol derivative. See: Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449-1456.
23. The addition of imine inhibits the coupling reaction; therefore, only 10 mol % imine was used.
24. 2 does not undergo exchange with free butene in solution. See: Whitesides, G. M.; Gaasch, J. F.; Stedronsky, E. R. J. Am. Chem. Soc. 1972, 94, 5258-5270.
25. Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163-1188.
26. Diamond, S. E.; Mares, F. J. Organomet. Chem. 1977, 142, C55-C57.
27. Hartwig, J. F.; Richards, S.; Baraño, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626-3633.
28. Murahashi, S. I.; Yoshimura, N.; Tsumiyama, T.; Kojima, T. J. Am. Chem. Soc. 1983, 105, 5002-5011.
29. Walker, H. W.; Kresge, C. T.; Ford, P. C.; Pearson, R. G. J. Am. Chem. Soc. 1979, 101, 7429-7430.
30. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
31. A similar Π-σ-Π equilibrium has been observed. See: Boone, B. J.; Klein, D. P.; Seyler, J. W.; Mendez, N. Q.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1996, 118, 2411-2421.
32. It is believed that Π-coordination in metal-imine complexes is required for insertion reactions to occur. See: Fryzuk, M. D.; Piers, W. E. Organomet. 1990, 9, 986-998.
33. Bryndza, H. E.; Calabrese, J. C.; Marsi, M.; Roe, D. C.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1986, 118, 4805-4813.
34. For example, when 2-phenylpyrrolidine and 4-bromobiphenyl were coupled using 2 mol % Pd2(DBA)3, 4 mol % (±)-BINAP, and 1.4 equiv of NaOt-Bu in toluene at 70 °C, a mixture of 46% 2-phenyl-1-pyrroline, 36% biphenyl, and 18% N-(p-biphenyl)-2-phenylpyrrolidine was obtained as determined by GC analysis. The percentages were corrected for the response factors of each component of the mixture.
35. McDermott, J. X.; White, J. F.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6521-6528.
36. Ma, D.; Yao, J. Tetrahedron: Asymm. 1996, 7, 3075-3078.
37. Verdaguer, X.; Lange, U. E.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784-6785.
38. Vedejs, E.; Gingras, M. J. Am. Chem. Soc. 1994, 116, 579-588.
39. Fry, D. F.; Fowler, C. B.; Dieter, R. K. SynLett 1994, 836-838.