Chiral bicyclic lactams. A new study on facial alkylation

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 5712-5713

  Meyers, A I ^a   Seefeld, M A ^a   Lefker, B A ^a  

^a Immunology and Pathology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.3.0]OCTANE DERIVATIVE; LACTAM DERIVATIVE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029819660     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960952g     Document Type: Article

References (8)

1. For a review on this subject, see: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. A discussion on the endo/exo selectivity is presented in this review (pp 9557-9564).
2. Liotta, D.; Durkin, K. A. J. Am. Chem. Soc. 1990, 112, 8162.
3. Thottathill, J. K.; Maniot, J. L.; Mueller, R. H.; Wong, M. K. Y.; Kissick, T. P. J. Org. Chem. 1986, 51, 3140.
4. Meyers, A. I.; Wanner, K. Th. Tetrahedron Lett. 1985, 26, 2047.
5. For a similar dramatic effect in changing from endo to exo alkylation see Roth, G. P.; Leonard, S. F.; Tong, L. J. Org. Chem. 1996, 61, XXXX. We thank Dr. Roth for sharing this information with us prior to publication.
6. In addition to models, some preliminary molecular modeling studies were also performed that further indicated the steric interference of an alkyl or aryl substituent to alkylation of the enolate carbon.
7. Evans, D. A.; Carroll, G. L.; Truesdale, L. K. J. Org. Chem. 1974, 39, 914.
8. Meyers, A. I.; Lefker, B. A.; Sowin, T. J.; Westrum, L. J. J. Org. Chem. 1989, 54, 4243.