Tandem allylboration-ring-closing metathesis reactions for the preparation of biologically active molecules

Pure and Applied Chemistry

Volumn 75, Issue 9, 2003, Pages 1263-1275

  Ramachandran, P Veeraraghavan ^a   Reddy, M Venkat Ram ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BORANE DERIVATIVE; ETHER DERIVATIVE; LACTAM DERIVATIVE; LACTONE DERIVATIVE;

ALLYLBORATION; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CONFERENCE PAPER; DRUG SYNTHESIS; MEDICINAL PLANT; PRIORITY JOURNAL; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 0141744564     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200375091263     Document Type: Conference Paper

References (50)

1. B. M. Mikhailov and Y. N. Bubnov. Izv. Akad. Nauk SSSR Ser. Khim. 1874 (1964).
2. B. M. Mikhailov and V. F. Pozdnev. Izv. Akad. Nauk SSSR Ser. Khim. 1477 (1967).
3. For reviews on allylboration, see: (a) P. V. Ramachandran. Aldrichim. Acta 35, 23 (2002);
4. (b) H. C. Brown and M. Zaidlewicz. Organic Syntheses via Boranes, Volume 2: Recent Developments, Aldrich Chemical Co. (2001);
5. (c) P. V. Ramachandran and H. C. Brown (Eds.). Organoboranes for Syntheses, ACS Symp. Ser. Vol. 783, American Chemical Society, Washington, DC (2001);
6. (d) D. S. Matteson. Stereodefined Synthesis with Organoboranes, Springer, Berlin (1995);
7. (e) H. C. Brown and P. V. Ramachandran. In Advances in Asymmetric Synthesis, Vol. 1, Chap. 5, A. Hassner (Ed.), JAI, Greenwich, CT (1995);
8. (f) H. C. Brown and P. V. Ramachandran. J. Organometal. Chem. 500, I (1995);
9. (g) H. C. Brown and P. V. Ramachandran. Pure Appl. Chem. 66, 201 (1994);
10. (h) H. C. Brown and P. V. Ramachandran. Pure Appl. Chem. 63, 307 (1991).
11. For reviews discussing asymmetric allylboration using chiral allylboronates, see: (a) R. W. Hoffmann, G. Neil, A. Schlapbach. Pure Appl. Chem. 62, 1993 (1990);
12. (b) R. W. Hoffmann. Pure Appl. Chem. 60, 123 (1988);
13. (c) R. W. Hoffmann. Angew. Chem., Int. Ed. Engl. 26, 489 (1987);
14. (d) R. W. Hoffmann. Angew. Chem., Int. Ed. Engl. 21, 555 (1982);
15. (e) W. R. Roush. In Methods of Organic Chemistry (Houben-Weyl), Vol. E 21, p. 1410 (1995);
16. (f) W. R. Roush. In Trends in Synthetic Carbohydrate Chemistry, ACS Symp. Ser. Vol. 386, D. Horton, L. D. Hawkin, McGarvey (Eds.), Chap. 14, American Chemical Society, Washington, DC (1989);
17. (g) W. R. Roush. In Comprehensive Organic Synthesis Vol. 2, B. M. Trost and I. Fleming (Eds.), Pergamon, Oxford (1991);
18. (h) For a review on α-substituted allylboronates, see: W. R. Roush. In Methods of Organic Chemistry (Houben-Weyl), Vol. E 21, p. 1462 (1995).
19. (a) R. W. Hoffmann and H. J. Zeiss. J. Org. Chem. 46, 1309 (1981);
20. (b) R. W. Hoffmann and H. J. Zeiss. Angew. Chem., Int. Ed. Engl. 18, 306 (1979).
21. H. C. Brown and K. S. Bhat. J. Am. Chem. Soc. 108, 293 (1986).
22. D. S. Matteson. Stereodefined Synthesis with Organoboranes, Springer, Berlin (1995).
23. R. W. Hoffmann and T. Herold. Chem. Ber. 114, 375 (1981).
24. H. C. Brown and P. K. Jadhav. J. Am. Chem. Soc. 105, 2092 (1983).
25. H. C. Brown, J. Chandrasekharan, P. V. Ramachandran. J. Am. Chem. Soc. 110, 1539 (1988).
26. U. S. Racherla, Y. Liao, H. C. Brown. J. Org. Chem. 57, 6614 (1992).
27. D. J. S. Kumar, S. Madhavan, P. V. Ramachandran, H. C. Brown. Tetrahedron Asym. 11, 4629 (2000).
28. H. C. Brown, K. S. Bhat, R. S. Randad. J. Org. Chem. 52, 319 (1987).
29. P. V. Ramachandran, G. M. Chen, H. C. Brown. Tetrahedron Lett. 38, 2417 (1997).
30. (a) G. M. Chen, P. V. Ramachandran, H. C. Brown. Angew. Chem., Int. Ed. Engl. 38, 825 (1999);
31. (b) S. Itsuno, K. Watanabe, K. Ito, A. A. ElShehawy, A. A. Sarhan. Angew. Chem., Int. Ed. Engl. 36, 109 (1997).
32. H. C. Brown, P. K. Jadhav, P. T. Perumal. Tetrahedron Lett. 25, 5111 (1984).
33. H. C. Brown and P. K. Jadhav. Tetrahedron Lett. 25, 1215 (1984).
34. P. V. Ramachandran, M. V. R. Reddy, P. Bodhuri, J. S. Chandra, H. C. Brown. Unpublished results.
35. D. A. Evans, G. C. Andrews, B. J. Buckwalter. J. Am. Chem. Soc. 96, 5560 (1974).
36. (a) R. W. Hoffmann and B. Kemper. Tetrahedron Lett. 22, 5263 (1981);
37. (b) P. G. M. Wuts and S. S. Bigelow. J. Org. Chem. 47, 2498 (1982).
38. H. C. Brown, P. K. Jadhav, K. S. Bhat. J. Am. Chem. Soc. 110, 1535 (1988).
39. P. V. Ramachandran, J. S. Chandra, M. V. R. Reddy. J. Org. Chem. 67, 7547 (2002).
40. H. C. Brown and G. Narla. J. Org. Chem. 60, 4686 (1995).
41. K. Fujita and M. Schlosser. Helv. Chim. Acta 65, 1258 (1982).
42. P. V. Ramachandran, M. V. R. Reddy, V. Rauniyar, K. Padiya, H. C. Brown. Unpublished results.
43. H. C. Brown, K. S. Bhat, R. S. Randad. J. Org. Chem. 52, 3701 (1987).
44. P. V. Ramachandran, M. V. R. Reddy, H. C. Brown. Tetrahedron Lett. 41, 583 (2000).
45. P. V. Ramachandran, M. V. R. Reddy, H. C. Brown. J. Ind. Chem. Soc. 739 (1999).
46. M. V. R. Reddy, A. J. Yucel, P. V. Ramachandran. J. Org. Chem. 66, 2512 (2001).
47. P. V. Ramachandran, M. V. R. Reddy, J. P. Rearick, N. Hoch. Org. Lett. 3, 19 (2001).
48. M. V. R. Reddy, P. V. Ramachandran, H. C. Brown. J. Organomet. Chem. 624, 239 (2001).
49. P. V. Ramachandran, M. V. R. Reddy, P. Bodhuri, J. S. Chandra. Unpublished results.
50. Contribution # 26 from the Herbert C. Brown Center for Borane Research.