The Mitsunobu reaction of ortho-ethers of secondary benzylic alcohols. Concise enantioselective synthesis of a key intermediate of the novel β-adrenergic receptor antagonist MY336-a

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5329-5332

  Kaufman, Teodoro S ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDRO 1,3 BIS(HYDROXYMETHYL) 7 METHOXY 6 METHYL 8 QUINOLINOL; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; TECHNIQUE;

EID: 0030598095     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01122-7     Document Type: Article

References (29)

1. 1. For leading reviews, see: (a) Mitsunobu, O. Synthesis 1981, 1-28;
2. (b) Castro, B. R. Org. Reactions 1983, 29, 1-162 ;
3. (c) Hughes, D. L. Org. Reactions 1992, 42, 335-656.
4. 2. Iida, H.; Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 1985, 26, 3255-3258.
5. 3. (a) Brown, R. F. C.; Jackson, W. R.; McCarthy, T. D. Tetrahedron Lett. 1993, 34, 1195-1196;
6. (b) ibid. Tetrahedron 1994, 50, 5469-5488.
7. 4. (a) Grunewald, G. L.; Paradkar, V. M.; Pazhenchevsky, B.; Pleiss, M. A.; Sall, D. J.; Seibel, W. L.; Reitz, T. J. J. Org. Chem. 1983, 48, 2321-2327;
8. (b) Grunewald, G. L.; Arlington, H. S.; Bartlett, W. J.; Reitz, T. J.; Sall, D. J. J. Med. Chem. 1986, 29, 1972-1982.
9. 5. Ku, T. W.; Kondrad, K. H.; Gelason, J. G. J. Org. Chem. 1989, 54, 3487-3491.
10. 6. (a) Rao, A. V. R.; Yadav, J. S.; Reddy, K. B.; Mehendale, A. R. J. Chem. Soc., Chem. Commun. 1984, 453-455;
11. (b) ibid. Tetrahedron 1984, 40, 4643-4647.
12. 7. Ponzo, V. L.; Kaufman, T. S. Tetrahedron Lett. 1995, 36, 9105-9108.
13. 8. (a) Kaufman, T. S. J. Chem. Soc., Perkin Trans. 1 1996, in the press;
14. (b) Kaufman, T. S. J. Chem. Soc., Perkin Trans. 1 1993, 403-404.
15. 9. Compounds 5a-c are commercially available. For the synthesis of 5d see Kaufman, T. S. Synth. Commun. 1992, 22, 1913-1921.
16. 10. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553;
17. (b) Mathre, D. J.; Thompson, A. S.; Douglas, A. W.; Hoogsteen, K.; Carroll, J. D.; Corley, E. G.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 2880-2888.
18. 11. Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017-3020.
19. 12. The reaction mechanism has been studied in depth. See (a) Adam, W.; Narita, N.; Nishizawa, Y. ibid. 1984, 106, 1843-1845;
20. (b) Varasi, M.; Walker, K. A. M.; Maddox, M. L. J. Org. Chem. 1987, 52, 4235-4238;
21. (c) Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487-6491;
22. (d) Camp, D.; Jenkins, I. D. J. Org. Chem. 1989, 54, 3045-3049.
23. 13C NMR resonances of the carbon atoms attached to the ortho oxygen [compare 6a (54.99), 6b (60.53), 6c (69.77) and 6d (74.56)]; see Kaufman, T. S.; Jürgens, A. R.; Sindelar, R. D. Magn. Reson. Chem., 1990, 1178-1181, and references cited therein.
24. 14. For an example and discussion on 3-substituents controlling the reactivity of ortho-alkoxy substituted benzaldehydes, see Jones, P. R.; Jaglowski, A. J., Jr. J. Org. Chem. 1990, 55, 3891-3896.
25. 15. Chen, C.-P; Prasad, K; Repic, O. Tetrahedron Lett. 1991, 32, 7175-7178.
26. [α]20D: +184.2 (c = 2.2).
27. 17. Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. J. Org. Chem. 1993, 58, 832-839.
28. 18. Tsunoda, T.; Yamamiya, Y.; Kawamura, Y.; Ito, S. Tetrahedron Lett. 1995, 36, 2529-2530.
29. 19. Edwards, M. L.; Stemerick, D. M.; McCarthy, J. R. Tetrahedron Lett. 1990, 31, 3417-3420.