Preparation of Cyclohexanones and Cyclopentanones of High Optical Purity

Journal of Organic Chemistry

Volumn 45, Issue 23, 1980, Pages 4699-4702

  Taber, Douglass F ^a   Saleh, Samir A ^a   Korsmeyer, Richard W ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000293569     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo01311a031     Document Type: Article

References (23)

1. Stork, G.; Takahashi, T.; Kawamoto, I.; Suzuki, T. J. Am. Chem. Soc. 1978, 100, 8272.
2. Fitzsimmons, B. J.; Fraser-Reid, B. J. Am. Chem. Soc. 1979, 101, 6125.
3. For a review, see: Valentine, D., Jr.; Scott, J. W. Synthesis 1978
4. Pirkle, W. H.; Rinaldi, P. L. J. Org. Chem. 1978, 43, 3803.
5. Meyers, A. I.; Slade, J.; Smith, R. K.; Mihelich, E. D.; Hershenson, F. M.; Liang, C. D. J. Org. Chem. 1979, 44, 2247.
6. Taber, D. F. J. Am. Chem. Soc. 1977, 99, 3513.
7. Trost, B. M.; Taber, D. F.; Alper, J. B. Tetrahedron Lett. 1976, 3857.
8. Clark, R. D.; Heathcock, C. H. Tetrahedron Lett. 1975, 529. Kondo, K.; Umemoto, T.; Takakatake, Y.; Tunemoto, D. Tetrahedron Lett. 1977, 113.
9. Mauz, O. Justus Liebigs Ann. Chem. 1974, 345.
10. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082.
11. Regitz, M.; Hocker, J.; Liedhegener, A. “Organic Syntheses”; Wiley: New York, 1973; Collect. Vol. V, p 197.
12. Nakazaki, M.; Naemura, K.; Nakahara, S. J. Org. Chem. 1979,44, 2438.
13. Still, W. C., Columbia University, personal communication.
14. Cyclohexanone 6 smeared substantially on TLC. This was not the case with cyclopen tan tone 13.
15. Krapcho, A. P.; Lovey, A. J. Tetrahedron Lett. 1973, 957.
16. Brown, H. C.; Subba Rao, B. C. J. Am. Chem. Soc. 1959,81, 6428.
17. Caine, D.; Pennington, W. R.; Smith, T. L., Jr. Tetrahedron Lett. 1978, 2663.
18. Tunemoto, D.; Araki, N.; Kondo, K. Tetrahedron Lett. 1977, 109.
19. Hunt, B. J.; Rigby, W. Chem. Ind. (London) 1967, 1869.
20. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
21. Targett, N. M.; Kilcoyne, J. P.; Green, B. J. Org. Chem. 1979, 44, 4962.
22. House, H. O.; Chu, C. Y.; Wilkins, J. M.; Umen, M. J. Org. Chem. 1975, 40, 1460.
23. Vogel, A. I. “Practical Organic Chemistry”, 3rd ed.; Logman: London, 1974; p 344.