A temporary phosphorus tether/ring-closing metathesis strategy to functionalized 1,4-diamines

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3939-3942

  Sprott, Kevin T ^a   McReynolds, Matthew D ^a   Hanson, Paul R ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE; PHOSPHORUS;

ARTICLE; CHEMISTRY;

DIAMINES; PHOSPHORUS; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0035969609     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016828n     Document Type: Article

References (55)

1. (a) Lam, P, Y. S.; Jadhav, P. K.; Eyermann, C. J.; Hodge, C. N.; Ru, Y.; Bacheler, L. T.; Meek, J. L.; Otto, M. J.; Rayner, M. M.; Wong, Y. N.; Chang, C.-H.; Weber, P. C.; Jackson, D. A.; Sharpe, T. R.; Erickson-Vittanen, S.; Science 1994, 263, 380-384.
2. (b) Patel, M.; Kaltenbach, R. F., III; Nugiel, D. A.; McHugh, R. J., Jr.; Jadhav, P. K.; Bacheler, L. T.; Cordova, B. C.; Klabe, R. M.; Erickson-Viitanen, S.; Garber, S.; Reid, C.; Seitz, S. P. Bioorg. Med. Chem. Lett. 1998, 8, 1077-1082.
3. (c) De Lucca, G. V J. Org. Chem. 1998, 63, 4755-4766.
4. (d) Hultén, J.; Bonham, N. M.; Nillroth, U.; Hansson, T.; Zuccarello, G.; Bouzide, A.; Åqvist, J.; Classon, B.; Danielson, U. H.; Karlén, A.; Kvarnström, I.; Samuelsson, B.; Hallberg, A. J. Med. Chem. 1997, 40, 885-897.
5. For examples of biologically active 1,4-diamines, see: (a) Rische, T.; Eilbracht, P. Tetrahedron 1999, 55, 3917-3922 and reft 1-4 cited therein.
6. (b) He, Z.; Nadkarni, D. V.; Sayre, L. M.; Greenaway, F. T. Biochim. Biophys. Acta 1995, 1253, 117-127.
7. For the use of 1,4-diamines as dipeptide isosteres, see:(c) Baker, W. R.; Condon, S. L. J. Org. Chem. 1993, 58, 3277-3284.
8. For examples of 1,4-diamines and their derivatives serving as ligands for metals, see: (a) Nivorozhkin, A. L.; Toftlund, H.; Jøergensen, P. L.; Nivorozhkin, L. E. J. Chem. Soc., Dalton Trans. 1996, 1215-1221.
9. (b) Fritsky, I. O.; Kozlowski, H.; Prisyazhnaya, E. V.; Karaczyn, A.; Kalihabchuk, V. A.; Glowiak, T. J. Chem. Soc., Dalton Trans. 1998, 1535-1536.
10. (c) Codina, G.; Caubet, A.; Lopez, C.; Moreno, V.; Molins, E. Helv. Chim. Acta 1999, 82, 1025-1037.
11. Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28-32.
12. (5l For recent reviews, see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
13. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043.
14. (c) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240.
15. (d) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
16. (e) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
17. (a) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769-1772.
18. (b) Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Synthesis 2001, 612-620 and references therein.
19. (c) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2001, 3, 3285-3288.
20. For a comprehensive review on disposable tethers, see: Gauthier, D. R., Jr.; Zandi, K. S.; Shea, K. J. Tetrahedron 1998, 54, 2289-2338.
21. For a review on temporary silicon-tethered (Si-tethered) reactions, see: (a) Fensterbank, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 8, 813-854.
22. For additional references on Si-tethered reactions, see: (b) Ishikawa, T.; Kudo, T.; Shigemori, K.; Saito, S. J. Am. Chem. Soc. 2000, 122, 7633-7637.
23. (c) Shuto, S.; Yahiro, Y.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 5547-5557.
24. (d) Miyata, O.; Nishiguchi, A.; Ninomiya, I.; Aoe, K.; Okamura, K.; Naito, T. J. Org. Chem. 2000, 65, 6922-6931.
25. (e) Rubinstenn, G.; Mallet J.-M.; Sinay, P. Tetrahedron Lett. 1998, 39, 3697-3700.
26. For examples of metal-derived temporary tethers, see the following. Mg and Al tethers: (a) Stork, G.; Chan, T. Y. J. Am. Chem. Soc. 1995, 117, 6595-6596.
27. Boron tethers: (b) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450-451.
28. Al and Zn tethers: (c) Bertozzi, F.; Olsson, R.; Frejd, T. Org. Lett. 2000, 2, 1283-1286.
29. For an example of a phosphoramidic P(V) temporary tether, see: Rubinstenn, G.; Esnault, J.; Mallet, J.-M; Sinay, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336. To the best of our knowledge, there are no examples in the literature of utilizing P(III) as a temporary tether.
30. For examples of silicon tethers utilized in the RCM reaction, see: (a) Evans, P. A.; Murthy, V. S. J. Org. Chem. 1998, 63, 6768-6769.
31. (b) Hoye, T. R.; Promo, M. A. Tetrahedron Lett. 1999, 40, 1429-1432.
32. (c) Gierasch, T. M.; Chytil, M.; Didiuk, M. T.; Park, J. Y.; Urban, J. J.; Nolan, S. P.; Verdine, G. L. Org. Lett. 2000, 2, 3999-4002.
33. (d) Lobbel, M.; Koll, P. Tetrahedron: Asymmetry 2000, 11, 393-396.
34. For other tethers utilized in the RCM reaction, see the following. Catechol tethers: (a) O'Leary, D. J.; Miller, S. J.; Grubbs, R. H. Tetrahedron Lett. 1998, 39, 1689-1690.
35. (b) Rodriguez, J. R.; Castedo, L.; Mascarenas, J. L. Org. Lett. 2000, 2, 3209-3212.
36. Phthalamide tethers: (c) Sprott, K. T.; Hanson, P. R. J. Org. Chem. 2000, 65, 7913-7918.
37. For other methods of producing simple, unsaturated 1,4-diamines, see: (a) Radhakrishnan, U.; Al-Masum, M.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 1037-1040.
38. (b) Courtois, G.; Desre, V.; Miginiac, L. J. Organomet. Chem. 1999. 580, 178-187. For a recent method of producing saturated 1,4-diamines, see ret 2a.
39. To the best of our knowledge, no general method exists for the preparation of nonracemic, differentially substituted 1,4-diamines.
40. We have reported the synthesis of 1,4-diamine 1a (Scheme 2) via a phthalamide tether/RCM/hydrolysis sequence. RCM yielded predominantly the Z-isomer (10:1 Z:E), see ref 12c.
41. For the first generation Grubbs catalyst, see: (a) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
42. (b) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041. For the second generation Grubbs catalyst, see:
43. (c) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
44. 1,3,2-Diazaphosphepine 2-oxide 10 hydrolyzed after prolonged storage at 0 °C (2-3 weeks).
45. 15a,b occurs in excellent yields with most substrates if the reaction was performed on small scale (<500 mg). Reaction times varied from 1 to 24 h.
46. No transesterification was observed during the tether cleavage procedure when benzyl esters were employed, as in 1c and 1d.
47. Details of the unsuccessful attempts with other tethers are provided in the Supporting Information.
48. Dougherty, J. M.; Probst, D. A.; Robinson, R. E.; Moore, J. D.; Klein, T. A.; Snelgrove, K. A.; Hanson, P. R. Tetrahedron 2000, 56, 9781-9790 and references therein.
49. (a) Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676-678.
50. (b) Saari, W. S., Fisher, T. E. Synthesis 1990, 453-454.
51. 3 to provide the corresponding phosphoramide, see:
52. (b) Burns, B.; Studley, J. R.; Wills, M. Tetrahedron Lett. 1993, 34, 7105-7106.
53. 3 occurs only once to give the phosphonamidic dichloridate, see ref 6b.
54. Sprott, K. T.; Hanson, P. R. J. Org. Chem 2000, 65, 4721-4728.
55. The unambiguous assignment of the major diastereomer, as well as mechanistic rationale for the observed selectivity, is currently being investigated.