Stereoselective alkylations in rigid systems. Effect of remote substituents on π-facial additions to lactam enolates. Stereoelectronic and steric effects

Journal of the American Chemical Society

Volumn 120, Issue 30, 1998, Pages 7429-7438

  Meyers, A I ^a   Seefeld, Mark A ^a   Lefker, Bruce A ^b   Blake, James F ^b   Williard, Paul G ^c  

^a Immunology and Pathology   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^c BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; LACTAM;

ALKYLATION; ARTICLE; CALCULATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032486779     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980614s     Document Type: Article

References (20)

1. (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503.
2. (b) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1.
3. Lefker, B. A. Ph.D. Thesis, Colorado State University, 1988.
4. Thottathil, J. K.; Moniot, J. L.; Mueller, R. H.; Yong, M. K. Y.; Kissick T. P. J. Org. Chem. 1986, 51, 3140.
5. (a) Brown, K. L.; Damm, L.; Dunitz, J. D.; Eschenmoser, A.; Hobl, R.; Kratky, C. Helv. Chim. Acra 1978, 61, 3108.
6. (b) Damm, L. G.; Eschenmoser, A. Ph.D. Dissertation, Eidgenossischen Technischen Hochscule, Zurich, Switzerland, 1979.
7. Meyers, A. I.; Seefeld, M. A.; Lefker B. A. J. Org. Chem. 1996, 61, 5712. See also: Roth, G.; Leonard, S. F.; Tong L. J. Org. Chem. 1996, 61, 5710.
8. Meyers, A. I.; Seefeld, M. A.; Lefker B. A. J. Org. Chem. 1996, 61, 5712. See also: Roth, G.; Leonard, S. F.; Tong L. J. Org. Chem. 1996, 61, 5710.
9. Meyers, A. I.; Seefeld, M. A.; Lefker, B. A.; Blake, J. F. J. Am. Chem. Soc. 1997, 119, 4565.
10. Liotta, D.; Durkin, K. A. J. Am. Chem. Soc. 1990, 112, 8162.
11. Meyers, A. I; Wallace, R. H.; Romo, D. Unpublished results.
12. Meyers, A I.; Wallace, R. H. J. Org. Chem. 1989, 54, 2509.
13. Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540.
14. Evans, D. A.; Carroll, G. L.; Truesdale, L. K. J. Org. Chem. 1974, 39, 914.
15. Meyers, A. I.; Harre, M.; Garland, R. J. Am. Chem. Soc. 1984, 106, 1146.
16. Meyers, A. I.; Wanner, K. Th. Tetrahedron Lett. 1985, 26, 2047.
17. Westrum, L. J.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 973.
18. Frisch, M. J.; Trucks. G. W.; Schlegel, H. B.; Gill. P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith. T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C, Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; HeadGordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
19. -1 were treated as classical rotations, while imaginary frequencies were ignored. Grev, R. S.; Janssen, C. L.; Schaefer, H. F., III. J. Chem. Phys. 1991, 95, 5128.
20. For a detailed discussion of this procedure, see: Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.