Synthesis and Reactions of α- (Trifluromethanesulfonyloxy) Enecarbamates Prepared from N-Acyllactams

Journal of Organic Chemistry

Volumn 60, Issue 9, 1995, Pages 2656-2657

  Foti, Christopher J ^a   Comins, Daniel L ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029014202     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00114a006     Document Type: Article

References (38)

1. Stang, P. J.; Summerville, R. J. Am. Chem. Soc. 1969, 91, 4600.
2. Ritter, K. Synthesis 1993, 735.
3. Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. R. Vinyl Cations, Academic: New York, 1979.
4. Hanack, M.; Subramanian, L. R. In Houben-weyl, 4th ed., Vol. E19c; Hanack, M., Ed., Thieme: Stuttgart, 1990; p 97.
5. Stang, P. J. Acc. Chem. Res. 1978, 11, 107.
6. Stang, P. J. In Houben-weyl, 4th ed., Vol. E19b; Regito, M., Ed.; Thieme: Stuttgart, 1989; p 14.
7. Stang, P. J.; Hanack, M. C.; Subramanian, L. R. Synthesis 1982, 85.
8. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
9. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
10. While this manuscript was in preparation, a single example appeared in the literature, see: Isobe, M.; Okita, T. Synlett 1994, 589.
11. Rubiralta, M.; Giralt, E.; Diez, A. Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives. In Studies in Organic Chemistry, Elsevier: New York, 1991; Vol. 43, Chapter 1.
12. Berrien, J.-F.; Royer, J.; Husson, H.-P. J. Org. Chem. 1994 59, 3769.
13. Aketa, K. I.; Terashima, S.; Yamada, S.-I. Chem. Pharm. Bull. 1976, 24, 621.
14. Kisfaludy, L.; Korenczki, F.; Katho, A. Synthesis 1982, 163.
15. Ohtani, B.; Tsuru, S.; Nishimoto, S.; Kagiya, T.; Izawa, K. J. Org. Chem. 1990, 55, 5551.
16. Seebach, D.; Dziadulewicz, E.; Behrendt, L.; Cantoreggi, S.; Fitzi, R. LiebigsAnn. Chem. 1989, 1215.
17. Copeland, T. D.; Wondrak, E. M.; Tozser, J.; Roberts, M. M.; Oroszlan, S. Biochem. Biophys. Res. Commun. 1990, 169, 310.
18. Kikumoto, R.; Tamao, Y.; Tezuka, T.; Tonomura, S.; Hara, H.; Ninomiya, K.; Hijikata, A.; Okamoto, S. Biochemistry 1984, 23, 85.
19. Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914.
20. Sahlberg, C. J. Labelled Compd. Radiopharm. 1987 24, 529.
21. Jones, T. K.; Mills, S. G.; Reamer, R. A.; Askin, D.; Desmond, R.; Volante, R. P.; Shinkai, I. J. Am. Chem. Soc. 1989, 111, 1157.
22. Sehgal, S. N.; Baker, H.; Eng, C. P.; Singh, K.; Veniza, C. J. Antibiot. 1983, 36, 352.
23. For a review on organometalic coupling reactions of enol triflates, see: Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47.
24. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1985, 26, 1109.
25. For examples, see: Noyori, R. In Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons, Inc.: New York, 1994; Chapter 2.
26. Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers, Inc.: New York, 1994; Chapter 2.
27. Armstrong, J. D., Ill; Eng, K. K.; Keller, J. L.; Purick, R. M.; Hartner, F. W., Jr.; Choi, W.-B.; Askin, D.; Volante, R. P. Tetrahedron Lett. 1994, 35, 3239.
28. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125.
29. Takaya, H.; Miyashita, A.; Noyori, R.; Souchi, T. Tetrahedron 1984, 40, 1245.
30. Noyori, R.; Ohkuma, T.; Kitamura, M. J. Am. Chem. Soc. 1987, 109, 5856.
31. For cleavage of phenyl carbamates using catalytic hydrogenation, see: Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1991, 32, 5697;
32. J. Chem. Soc, Chem. Commun. 1993, 58, 7732.
33. Al-awar, R. S.; Joseph, S. P.; Comins, D. L. J. Org. Chem. 1993, 58, 7732.
34. Perumattam, J.; Shearer, B. G.; Confer, W. L.; Matthew, R. M. Tetrahedron Lett. 1991, 32, 7183.
35. Zacharius, R. M.; Thompson, J. F.; Steward, F. C. J. Am. Chem. Soc. 1952, 74, 2949.
36. Meyers, A. I.; Edwards, P. D.; Bailey, T. R.; Jagdmann, G. E., Jr. J. Org. Chem. 1985, 50, 1019.
37. Comins, D. L.; Weglarz, M. A. J. Org. Chem. 1991, 56, 2506.
38. Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109.