Letters in organic chemistry hydroiodination of terminal double bonds via hydroboration or hydrozirconation in connection with the total synthesis of fluvirucins

Letters in Organic Chemistry

Volumn 3, Issue 3, 2006, Pages 183-186

  Freixas, Glòria ^a   Urpí, Fèlix ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Hydroboration; Hydroiodination; Hydrozirconation; Sch 38516 Sch 38518; Schwartz's reagent

Indexed keywords

EID: 33746164737     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806775789895     Document Type: Article

References (30)

1. 1 aglycon);
2. 1);
3. 1 aglycon);
4. 1 aglycon);
5. 1 aglycon).
6. a) Martín, M.; Mas, G.; Urpi, F.; Vilarrasa, J. Angew. Chem. Int. Ed. 1999, 38, 3086 (Sch 38516 aglycon);
7. b) Espasa, G. Master Thesis (Synthesis of Sch 38518 Macrolactam), Universitat de Barcelona, 2000.
8. Recent reviews on hydroboration: a) Crudden, C. M.; Edwards, D. Eur. J. Org. Chem 2003, 4695;
9. b) Ramachandran, P. V.; Brown, H. C. ACS Symp. Ser. 2001, Vol. 783, pp. 1-15;
10. c) Hayashi, T. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, pp. 251-364.
11. Reviews on the hydrozirconation reaction and it's synthetic applications: a) Wipf, P.; Kendall, C. Topics Organomet. Chem. 2004, 8, 1;
12. b) Lipshutz, B. H.; Pfeiffer, S. S.; Noson, K.; Tomioka, T. In Titanium and Zirconium in Organic Synthesis; Wiley-VCH: Weinheim, 2002; pp. 110-148;
13. c) Wipf, P.; Takahashi, H; Zhuang, N. Pure & Appl. Chem. 1998, 70, 1077;
14. d) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853;
15. e) Labinger, J. A. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8, pp. 667-702;
16. f) Negishi, E.; Takahashi, T. Synthesis 1988, 1.
17. For the advantages of the borane-N-ethyl-N-isopropil complex, see: Brown, H. C.; Kanth, J. V. B.; Zaidlewicz, M. Tetrahedron 1999, 55, 5991.
18. Iodination conditions according to: Kabalka, G. W.; Sastry, K. A. R; Sastry, K. U. Synth. Commun. 1992, 12, 101.
19. Checked by HPLC with a CHIRALPAK AD-H column (99:1 hexane-isopropanol as the eluent in the case of 5c; hexane in the case of 5d).
20. a) Evans, D. A.; Bender, S. L.; Morris, J.; J. Am Chem. Soc. 1988, 110, 2506;
21. b) Evans, D. A.; Rieger, D. L.; Jones, T. K, Kaldor, S. W. J. Org. Chem. 1990, 55, 6260.
22. Previous example of the reduction of an acyl oxazolidone to aldehyde with the Schwartz reagent: White, J. M.; Tunoori, A. R; Georg, G. I. J. Am. Chem. Soc. 2000, 122, 11995.
23. For a very recent review on catalyzed hydrometallations, see: Makba, R; Negishi, E. Handbook of Organopalladium Chemistry for Orgardc Synthesis 2002; Vol. 2, pp. 2789-2823.
24. a) Alvhaell, J.; Gronowitz, S.; Hallberg, A.; Svenson, R. J. Am. Oil Chem Soc. 1984, 61, 430;
25. b) Svenson, R.; Gronowitz, S. Chem. Scr., 1982, 19, 149;
26. c) Schwartz, J.; Labinger, J. A. Angew. Chem. 1976, 88, 402.
27. iBuCl, catalyzed by Lewis acids, have been reported: Makabe, H.; Negishi, E. Eur. J. Org. Chem. 1999, 969.
28. 2-bis(oxazoline) complexes to block the CO groups of 3c, aimed at enhancing the chances of the C-C double bond hydrozirconation, but a redox process took place preferably.
29. For the preparation in situ of Schwartz's reagent, see: a) Lipshutz, B. H.; Keil, R.; Ellsworth, E. L. Tetrahedron Lett. 1990, 31, 7257, and references therein. Also see:
30. b) Alvhaell, J.; Gronowitz, S.; Hallberg, A. Chem. Scr., 1988, 28, 285.