Diastereoselective palladium-catalyzed α-arylation of 4-substituted cyclohexyl esters

Organic Letters

Volumn 10, Issue 22, 2008, Pages 5251-5254

  Bercot, Eric A ^a   Caille, Seb ^a   Bostick, Tracy M ^a   Ranganathan, Krishnakumar ^a   Jensen, Randy ^a   Faul, Margaret M ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61349203786     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8021758     Document Type: Article

References (47)

1. For reviews, see: (a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401.
2. (b) Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597.
3. (c) Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363-5367.
4. For a review on the use of chiral bicyclic lactam auxiliaries, see: (a) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873.
5. For a review on enolate alkylation stratergies, see: (b) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105-10146.
6. (c) Eames, J.; Suggate, M. J. Angew. Chem., Int. Ed. 2005, 44, 186-189.
7. (d) Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688-1690.
8. (a) Piers, E.; Marais, P. C. J. Org. Chem. 1990, 55, 3454-3455.
9. (b) Chieffi, A.; Kamikawa, K.; Ahman, J.; Fox, J. M.; Buchwald, S. L. Org. Lett. 2001, 3, 1897-1900.
10. (c) Huang, J.; Bunel, E.; Faul, M. M. Org. Lett. 2007, 9, 4343-4346.
11. For seminal examples of ketone arylation, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109.
12. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383.
13. (c) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740-1742.
14. For recent reviews on Pd-catalyzed arylation of carbonyl compounds, see: (a) Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2002, 41, 953-956.
15. (b) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
16. For stereoselective approaches to a similar 4-substituted cyclohexane core, see: (a) Scott, J. P.; Lieberman, D. R.; Beureux, O. M.; Brands, K. M. J.; Davies, A. J.; Gibson, A. W.; Hammond, D. C.; McWilliams, C. J.; Stewart, G. W.; Wilson, R. D.; Dolling, U.-H. J. Org. Chem. 2007, 72, 4149-4155.
17. (b) Davies, A. J.; Scott, J. P.; Bishop, B. C.; Brands, K. M. J.; Brewer, S. E.; DeSilva, J. O.; Dormer, P. G.; Dolling, U.-H.; Gibb, A. D.; Hammond, D. C.; Lieberman, D. R.; Palucki, M.; Payack, J. F. J. Org. Chem. 2007, 72, 4864-4871.
18. The Pd-catalyzed arylation of 4-methylcyclohexyl esters has been reported but no selecitvity data was provided; see: John, V.; Maillard, M.; Tucker, J.; Jagodzinske, B.; Brogley, L.; Tung, J.; Shah, N.; Neitz, J. R. 2005, WO 05087752.
19. For selected examples of diastereoselective intramolecular Pd-catalyzed α-arylation reactions, see: (a) Reisman, S. E.; Ready, J. M.; Weiss, M. M.; Hasuoka, A.; Hirata, M.; Tamaki, K.; Ovaska, T. V.; Smith, C. J.; Wood, J. L. J. Am. Chem. Soc. 2008, 130, 2087-2100.
20. (b) MacKay, J. A.; Bishop, R. L.; Rawal, V. H. Org. Lett. 2005, 7, 3421-3424.
21. (c) Sole, D.; Vallverdu, L.; Solans, X.; Font-Bardia, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587-1594.
22. (d) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355-2358.
23. (e) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581-7582.
24. For selected examples of diastereoselective intermolecular α-aryaltion reactions, see: (f) Iwama, T.; Rawal, V. H. Org. Lett. 2006, 8, 5725-5728.
25. (g) Konopelski, J. P.; Lin, J.; Wenzel, P. J.; Deng, H.; Elliot, G. I.; Gerstenberger, B. S. Org. Lett. 2002, 4, 4121-4124.
26. (h) Elliott, G. I.; Konopelski, J. P.; Olmstead, M. M. Org. Lett. 1999, 1, 1867-1870.
27. (a) Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 5816-5817.
28. (b) Culkin, D. A.; Hartwig, J. F. Organometallics 2004, 23, 3398-3416.
29. The trans and cis descriptor refer to the relationship between the carbonyl functional group present on the fully substituted carbon atom and the substituent at the 4-position.
30. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley and Sons: New York, 1994; pp 686-771.
31. For the diastereoselective alkylation of 4-substituted cyclohexyl carbonyl derivatives, see: (a) House, H. O.; Bare, T. M. J. Org. Chem. 1968, 33, 934-949.
32. (b) Ziegler, F. E.; Wender, P. A. J. Org. Chem. 1977, 42, 2001-2002.
33. (c) Krapcho, A. P.; Dundulis, E. A. J. Org. Chem. 1980, 45, 3236-3245.
34. We postulated that not only should the equilibrium favor complex C, but reductive elimination from C to 1 should proceed via a lower energy transition state versus the reductive elimination of B to 4.
35. Cyclohexyl ester 2 was accessed in two steps from commercially available materials and used as a 2:1 mixture of isomers.
36. Commercially available from Johnson Matthey (CAS no. 185812-86-6; catalog no. Pd-113).
37. For recent reports detailing the use of this catalyst, see: (a) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 2002, 41, 4746-4748.
38. (b) Hama, T.; Liu, X.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 11176-11177.
39. (c) Hama, T.; Hartwig, J. F. Org. Lett. 2008, 10, 1545-1548.
40. (d) Hama, T.; Hartwig, J. L. Org. Lett. 2008, 10, 1549-1552.
41. Jørgensen, M.; Lee, S.; Liu, X.; Wolkowski, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 12557-12565.
42. (a) Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 10718-10719.
43. (b) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
44. Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996-8002.
45. 3 group is estimated to be isosteric with -i-Pr; see: Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 101, 6119-6146, and references therein.
46. The major diastereomer is the product resulting from the reductive elimination of an intermediate in which the palladium and methyl substituents are both disposed in equatorial positions in analogy to the arylated products obtained in the 4-substituted series.
47. 3 = 2.4-2.5; -OMe = 0.55-0.75.