An exceptionally reactive phosphotriester

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 347-350

  Moss, Robert A ^a   Bose, Susmita ^a   Ragunathan, Kaliappa G ^a   Jayasuriya, Nilu ^a   Emge, Thomas J ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; PHOSPHATE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0032576837     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10517-2     Document Type: Article

References (41)

1. (1) Rutgers Undergraduate Research Fellow.
2. (2) Reviews: (a) Segues, B.; Perez, E., Rico-Lattes, I.; Riviere, M.; Lattes, A. Bull. Soc. Chim. France 1996, 133, 925.
3. (b) Yang, Y-C. Chem. Ind. (London), 1 May 1995, 334.
4. (c) Yang, Y-C.; Baker, J.A; Ward, J.R Chem. Rev. 1992, 92, 1729.
5. (d) Pearson, G. Chem. Brit. Oct. 1995, 782.
6. (3) (a) Yang, Y-C.; Berg, F.J.; Szafraniec, L.L.; Beaudry, W.T.; Bunton, C.A.; Kumar, A. J. Chem. Soc. Perkin Trans. 2 1997, 607.
7. (b) Bhattacharya, S.; Snehalatha, K. J. Org. Chem. 1997, 62, 2198.
8. (c) Toullec, J.; Moukawim, M. Chem. Commun. 1996, 221.
9. (d) Bunton, C.A.; Foroudian, H.J. Langmuir 1993, 9, 2832.
10. (e) Yang, Y-C.; Szafraniec, L.L.; Beaudry, W.T.; Bunton, C.A. J. Org. Chem. 1993, 58, 6964.
11. (4) (a) Moss, R.A.; Kotchevar, A.T.; Park, B.D.; Scrimin, P. Langmuir 1996, 12, 2200.
12. (b) Moss, R.A.; Bose, S. Tetrahedron Lett. 1997, 38, 965.
13. (c) Berg, F.J.; Moss, R.A.; Yang, Y-C.; Zhang, H. Langmuir 1995, 11, 411.
14. (d) Moss, R. A.; Bracken, K.; Emge, T.J. J. Org. Chem. 1995, 60, 7739.
15. (5) (a) Scrimin, P.; Ghirlanda, G.; Tecilla, P.; Moss, R.A. Langmuir 1996, 12, 6235.
16. (b) Kimura, E; Hashimoto, H.; Koike, T. J. Am. Chem. Soc. 1996, 118, 10963.
17. (c) Weijnen, J.G.J.; Engbersen, J.F.J. Rec. Trav. Chim. 1993, 112, 351.
18. (d) Gellman, S.H.; Petter, R.; Breslow, R. J. Am. Chem. Soc. 1986, 108, 2388.
19. (e) Menger, F.M.; Gan, L.H.; Johnson, E.; Durst, H.D. J. Am. Chem. Soc. 1987, 109, 2800.
20. (6) Vanhooke, J.L.; Benning, M.W.; Raushel, P.M.; Holden, H.M. Biochem. 1996, 35, 6020. Benning, M.W.; Kuo, J.M.; Raushel, F.M.; Holden, H.M. Ibid. 1994, 33, 15001.
21. (6) Vanhooke, J.L.; Benning, M.W.; Raushel, P.M.; Holden, H.M. Biochem. 1996, 35, 6020. Benning, M.W.; Kuo, J.M.; Raushel, F.M.; Holden, H.M. Ibid. 1994, 33, 15001.
22. (7) Weiner, D.P.; Weimann, T.; Wolfe, M.M.; Wentworth, P., Jr.; Janda, K.D. J. Am. Chem. Soc. 1997, 119, 4088. Lavey, B.J.; Janda, K.D. J. Org. Chem. 1996, 61, 7633. Rosenblum, J.S.; Lo, L-C.; Li, T.; Janda, K.D.; Lerner, R.A. Angew. Chem. Int. Ed. (Engl.) 1995, 34, 2275.
23. (7) Weiner, D.P.; Weimann, T.; Wolfe, M.M.; Wentworth, P., Jr.; Janda, K.D. J. Am. Chem. Soc. 1997, 119, 4088. Lavey, B.J.; Janda, K.D. J. Org. Chem. 1996, 61, 7633. Rosenblum, J.S.; Lo, L-C.; Li, T.; Janda, K.D.; Lerner, R.A. Angew. Chem. Int. Ed. (Engl.) 1995, 34, 2275.
24. (7) Weiner, D.P.; Weimann, T.; Wolfe, M.M.; Wentworth, P., Jr.; Janda, K.D. J. Am. Chem. Soc. 1997, 119, 4088. Lavey, B.J.; Janda, K.D. J. Org. Chem. 1996, 61, 7633. Rosenblum, J.S.; Lo, L-C.; Li, T.; Janda, K.D.; Lerner, R.A. Angew. Chem. Int. Ed. (Engl.) 1995, 34, 2275.
25. (8) Bunton, C.A.; Robinson, L. J. Org. Chem. 1969, 34, 773.
26. (9) See: (a) Fendler, J.H.; Fendler, E.J. Catalysis in Micellar and Macromolecular Systems; Academic: New York, 1975, pp. 150-161.
27. (b) Moss, R.A.; Ihara, Y. J. Org. Chem. 1983, 48, 588.
28. (10) The diol (mp 138-140 °C) was obtained by basic cleavage of 1,8-naphthosultone: Erdmann, H. Ann. 1888, 247, 306.
29. (11) See below; details of the X-ray structure are available on request.
30. (12) Moss, R.A.; Alwis, K.W.; Shin, J-S. J. Am. Chem. Soc. 1984, 106, 2651.
31. (13) Moss, R.A.; Zhang, H.; Chatterjee, S.; Krogh-Jespersen, K. Tetrahedron Lett. 1993, 34, 1729.
32. (14) Oh, S.J.; Kyong, H.S.; Park, J.W. Chem. Commun. 1995, 575.
33. (15) (a) A brief summary can be found in ref. 3a.
34. (b) Thatcher, G.R.J.; Kluger, R. Adv. Phys. Org. Chem. 1989, 25, 99.
35. (c) Ba-Saif, S.A.; Waring, M.A.; Williams, A. J. Am. Chem. Soc. 1990, 112, 8115.
36. (d) Williams, A. Adv. Phys. Org. Chem. 1992, 27, 1.
37. (e) Gorenstein, D.G.; Chang, A.; Yang, J-C. Tetrahedron 1987, 43, 469.
38. 1/c; Mo Kα radiation, λ = 0.71073 Å; a = 8.795(1) Å, b = 13.024(2) Å, c = 26.279(3)Å, β = 90.97(1)°, z = 8; the final R(F) for 2486 observations with I > 2 σ > (I) was 0.038.
39. (17) Putative pseudorotation (if the TBP is an intermediate) of the naphthalenedioxy unit (from eqeq to apeq) would reduce the O2-P1-O3 angle to 90°, also incurring strain.
40. (18) Cf., Taylor, S.D.; Kluger, R. J. Am. Chem. Soc. 1992, 114, 3067.
41. (19) Wroblewski, A.E.; Verkade, J.G. J. Am. Chem. Soc. 1996, 118, 10168.