Selective reductions. XX. Stereochemistry of the Reduction of Cyclic, Bicyclic, and Polycyclic Ketones by Dialkylboranes. A Simple, Convenient Procedure for the Reduction of Ketones to the Corresponding Alcohols with Exceptionally High Steric Control

Journal of Organic Chemistry

Volumn 39, Issue 12, 1974, Pages 1631-1636

  Brown, Herbert C ^a   Varma, Vijaya ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000117392     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00925a006     Document Type: Article

References (42)

1. J. D. Morrison and H. S. Mosher, “Asymmetric Organic Reactions,” Prentice-Hall, Englewood Cliffs, N. J., 1971, pp 84-132.
2. A. V. Kamernltzky and A. A. Akhrem, Tetrahedron, 18, 705 (1962).
3. O. H. Wheeler and J. L. Mateos, Can. J. Chem., 36, 1431 (1958).
4. S. Beckmann and R. Mezger, Ber., 89, 2738 (1956).
5. H. C. Brown and H. R. Deck, J. Amer. Chem. Soc., 87, 5620 (1965).
6. W. G. Dauben, G. J. Fonken, and D. S. Noyce, J. Amer. Chem. Soc., 78, 2579 (1956).
7. J. C. Richer, J. Org. Chem., 30, 324 (1965).
8. H. Haubenstock and E. L. Eliel, J. Amer. Chem. Soc., 84, 2363 (1962).
9. J. Klein, E. Dunkelblum, E. L. Eliel, and Y. Senda, Tetrahedron Lett., 6127 (1968).
10. E. L. Eliel and Y. Senda, Tetrahedron, 26, 2411 (1970).
11. M. Cherest and H. Felkin, Tetrahedron Lett., 2205 (1968).
12. J. A. Marshall and R. D. Carroll, J. Org. Chem., 30, 2748 (1965).
13. E. C. Ashby, J. R. Boone, and J. P. Oliver, J. Amer. Chem. Soc., 95, 5427 (1973).
14. J. Klein, Tetrahedron Lett., 4307 (1973).
15. W. Huckel and J. W. Schter, Justus Liebigs Ann. Chem., 672, 62 (1964).
16. E. C. Ashby, J. P. Sevenair, and R. R. Dobbs, J. Org. Chem., 36, 197 (1971).
17. H. C. Brown, “Boranes in Organic Chemistry,” Cornell University Press, Ithaca, N. Y., 1972, pp 281-301.
18. H. C. Brown, P. Heim, and N. M. Yoon, J. Amer. Chem. Soc., 92, 1637 (1970).
19. H. C. Brown, D. B. Bigley, S. K. Arora, and N. M. Yoon, J. Amer. Chem. Soc., 92, 7161 (1970).
20. H. C. Brown, P. Heim, and N. M. Yoon, J. Org. Chem., 37, 2942 (1972).
21. H. C. Brown and V. Varma, J. Amer. Chem. Soc., 88, 2871 (1966).
22. H. C. Brown and W. C. Dickason, J. Amer. Chem. Soc., 92, 709 (1970).
23. E. J. Corey and R. K. Varma, J. Amer. Chem. Soc., 93, 7319 (1971).
24. H. C. Brown and S. Krishnamurthy, J. Amer. Chem. Soc., 94, 7159 (1972).
25. E. J. Corey, K. B. Becker, and R. K. Varma, J. Amer. Chem. Soc., 94, 8616 (1972).
26. C. A. Brown, J. Amer. Chem. Soc., 95, 4100 (1973).
27. G. Zweifel and H. C. Brown, J. Amer. Chem. Soc., 85, 2066 (1963).
28. G. Zweifel, N. R. Ayyangar, and H. C. Brown, J. Amer. Chem. Soc., 85, 2072 (1963).
29. H. C. Brown and D. B. Bigley, J. Amer. Chem. Soc., 83, 3166 (1961).
30. K. R. Varma and E. Caspi, Tetrahedron, 24, 6365 (1968).
31. Y. Kawazoa, Y. Sato, T. Okamoto, and K. Tsuado, Chem. Pharm. Bull., 11, 329 (1963).
32. J. Tadanier and W. Cole, J. Org. Chem., 27, 4610 (1962).
33. C. W. Shoppee and G. H. R. Summers, J. Chem. Soc., 3361 (1952).
34. E. M. Kosower and S. Winstein, J. Amer. Chem. Soc., 78, 4347 (1956).
35. G. Zweifel and H. C. Brown, Org. React., 13, 1 (1963).
36. H. C. Brown and R. L. Sharp, J. Amer. Chem. Soc., 90, 2915 (1968).
37. H. C. Brown and C. P. Garg, J. Amer. Chem. Soc., 83, 2952 (1961).
38. H. C. Brown, C. P. Garg, and K.-T. Liu, J. Org. Chem., 36, 387 (1971).
39. V. Varma, Ph D. Thesis, Purdue University, West Lafayette, Ind., 1967.
40. W. Huckel, M. Maier, E. Jordan, and W. Seegar, Justus Liebigs Ann. Chem., 616, 46 (1958).
41. W. Hückel, M. Maier, E. Jordan, and W. Seeger, Justus Liebigs Ann. Chem., 616, 46 (1958).
42. C. J. Kim and H. C. Brown, J. Amer. Chem. Soc., 94, 5043 (1972).