Enantioselective synthesis of cyclic amides and amines through Mo-catalyzed asymmetric ring-closing metathesis

Journal of the American Chemical Society

Volumn 127, Issue 23, 2005, Pages 8526-8533

  Sattely, Elizabeth S ^a   Alexander Cortez, G ^a   Moebius, David C ^a   Schrock, Richard R ^b   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; OLEFINS; SYNTHESIS (CHEMICAL);

BUCYCLIC STRUCTURES; CYCLIC AMIDES; CYCLIC AMINES; ENANTIOSELECTIVE SYNTHESIS;

AMINES;

ALKENE DERIVATIVE; AMIDE; AMINE; CYCLIC ALKENE; CYCLIC AMIDE; CYCLIC AMINE; MOLYBDENUM; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY; RING CLOSING METATHESIS; SYNTHESIS;

AMIDES; AMINES; CATALYSIS; CYCLIZATION; MODELS, MOLECULAR; MOLYBDENUM; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 20444452821     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051330s     Document Type: Article

References (53)

1. For reviews regarding enantioselective synthesis of amines, see: (a) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946.
2. (b) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094.
3. (c) Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953-2989.
4. For representative recent reports, see: (d) Denmark, S. E.; Stiff, C. M. J. Org. Chem. 2000, 65, 5875-5878.
5. (e) Fujihara, H.; Nagai, K.; Tomioka, K. J. Am. Chem. Soc. 2000, 122, 12055-12056.
6. (f) Dahmen, S.; Brase, S. J. Am. Chem. Soc. 2002, 124, 5940-5941.
7. (g) Hermanns, N.; Dahmen, S.; Bolm, C.; Brase, S. Angew. Chem., Int. Ed. 2002, 41, 3692-3694.
8. (h) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995.
9. (i) Boezio, A. A.; Charrette, A. B. J. Am. Chem. Soc. 2003, 125, 1692-1693.
10. (j) Berger, R.; Duff, K.; Leighton, J. L. J. Am. Chem. Soc. 2004, 126, 5686-5687.
11. (l) Keith, J. M.; Jacobsen, E. N. Org. Lett. 2004, 6. 153-155.
12. (l) Liu, X.; Li, H.; Deng, L. Org. Lett. 2005, 7, 167-169.
13. For example, see: (a) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 984-985.
14. (b) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193.
15. (c) Akullian, L. C.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4244-4247.
16. (d) Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 3734-3735.
17. (e) Mampreian, D. M.; Hoveyda, A. H. Org. Lett. 2004, 6, 2829-2832.
18. (f) Wu, J.; Mampreian, D. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 4584-4585.
19. For example, see: Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4018-4019.
20. For a review on Mo-catalyzed enantioselective olefin metathesis, see: Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
21. For a review on synthesis of N-containing compounds through catalytic olefin metathesis, see: (a) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238. For a review on catalytic RCM in alkaloid synthesis, see:
22. (b) Felpin, F. X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693-3712.
23. For Mo-catalyzed ARCM, see: (a) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 720, 4041-4142.
24. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda. A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721.
25. (c) Weatherhead, G. S.; Houser, J. H.; Ford, J. G.; Jamieson, J. Y.; Schrock, R. R.; Hoveyda, A. H. Tetrahedron Lett. 2000, 41, 9553-9559.
26. (d) Cefalo, D. R.; Kiely, A. F.; Wuchrer, M.; Jamieson, J. Y.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 3139-3140.
27. (e) Kiely, A. F.; Jernelius, J. A.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 2868-2869.
28. (f) Teng, X.; Cefalo, D. R.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 10779-10784.
29. For Ru-catalyzed ARCM, see: (a) Seiders. T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225-3228.
30. (b) VanVeldhuizen, J. J.; Gillingham, D. G.; Garber, S. B.; Kataoka, O.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 12502-12508.
31. (a) Dolman, S. J.; Sattely, E. S.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 2002. 124, 6991-6997.
32. (b) Dolman, S. J.; Schrock, R. R.; Hoveyda, A. H. Org. Lett. 2003, 5, 4899-4902.
33. For initial key reports on the use of Mo-catalyzed RCM to synthesize N-containing cyclic structure;, see: (a) Fu, G. C.; Grubbs. R. H. J. Am. Chem. Soc. 1992, 114, 4324-7325.
34. (b) Houri, A. F.; Xu, Z. M.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944.
35. (c) Martin, S. F.; Chen, H.-J.; Ccurtney, A. K.; Liao, Y.; Patzel, M.; Ramser. M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251-7264.
36. Morita, H.; Arisaka, M.; Yoshida, N.; Kobayashi, J. Tetrahedron 2000, 56, 2929-2934.
37. Morita, H.; Arisaka, M.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 2000, 65, 6241-6245.
38. Ye, Y.; Qin, G.-W.; Xu, R.-S. J. Nat. Prod. 1994, 57, 665-669.
39. Bubnov, Y. N.; Pastukhov, F. V.; Yampolsky, I. V.; Ignatenko, A. V. Eur. J. Org. Chem. 2000, 1503-1505.
40. Brown, H. C.; Racherla, U. S. J. Org. Chem. 1986, 51, 427-432.
41. For a discussion of catalyst generality as a function of substrate structure, see: Hoveyda, A. H. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, 2002; pp 991-1016.
42. For an alternative approach to enantioselective synthesis of this class of bicyclic amides, see: Groaning, M. D.; Meyers, A. I. Chem. Commun. 2000, 1027-1028.
43. For isolation and characterization of a disubstituted Mo-based alkylidene complex, see: Schrock, R. R.; DePue, R.; Feldman, J.; Schaverien, C. J.; Dewan, J. C.; Liu, A. H. J. Am. Chem. Soc. 1988, 110, 1423-1435.
44. Typically, homodimer formation is detected in all cases. However, in the more desirable instances, the chiral catalyst converts such compounds to the ARCM products (homodimers detected if reaction mixture is spectroscopically monitored).
45. For another study where electron-deficient Mo alkylidenes exhibit lower reactivity than their more electron-rich counterparts, see: La. D. S.; Sattely. E. S.; Ford, J. G.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 7767-7778.
46. For instances where similar Mo-based internal chelates have been proposed, see: (a) Fox, H. H.; Lee, J.-K.; Park, L. Y.; Schrock. R. R. Organometallics 1993, 12, 759-768.
47. (b) ref 9a.
48. For recent reviews of metal-catalyzed kinetic resolutions, see: (a) Hoveyda, I A. H.; Didiuk, M. T. Curr. Org. Chem. 1998, 2, 537-574.
49. (b) Cook, G. R. Curr. Org. Chem. 2000, 4, 869-885.
50. (c) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal 2001, 1, 5-26.
51. For use of borane-protected phosphines in catalytic RCM, see: Slinn. C. A.; Redgrave, A. J.; Hind, S. L.; Edlin. C.; Nolan, S. P.; Gouvernour, V. Org. Biomol. Chem. 2003, 1, 3820-3825.
52. Olefin hydrogenation in the presence of Wilkinson's catalyst is required before Pd-catalyzed debenzylation, since the latter conditions give rise to substantial amounts of C-N bond cleavage.
53. Since the majority of the substrates used in this study are solids or semisolids, Mo-catalyzed ARCM reactions cannot be carried out easily in the absence of solvent. In one representative case, the reaction mixture had to be heated to achieve dissolution of the catalyst sample, leading to significant lowering of product optical purity (reaction of ISb without solvent at 80 °C afforded 24 in 75% ee and 62% isolated yield vs 98% ee and 88% yield at 22 0C in benzene).