Remote chiral induction in the thio-Claisen rearrangement of bicyclic thiolactams

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 815-818

  Watson, Daniel J ^a   Lawrence, Charles M ^a   Meyers, A I ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM DERIVATIVE; OXAZOLIDINE DERIVATIVE; PIPERIDONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034606972     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02199-1     Document Type: Article

References (12)

1. (a) Romo, D.; Meyers, A. I. Tetrahedron 1985, 41, 5061.
2. (b) Brengal, G. P.; Meyers, A. I. Chem. Commun. 1997, 1.
3. (a) Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633.
4. (b) Lemieux, R. M.; Meyers, A. I. J. Am. Chem. Soc. 1998, 120, 5453.
5. (c) Lemieux, R. M.; Devine, P. N.; Mechelke, M. F.; Meyers, A. I. J. Org. Chem. 1998, 64, 3585.
6. (a) Cava, M. P.; Levinson, M. I. Tetrahedron 1985, 41, 5061.
7. (b) Lajoie, G.; Lepine, F.; Maziak, L.; Belleau, B. Tetrahedron 1983, 24, 3815.
8. Munchhof, M. J.; Devine, P. D.; Meyers, A. I. Unpublished results.
9. 6 according to the synthetic sequence shown below. Lactam 14 was prepared utilizing the same synthetic sequence and with comparable yields. (Equation Presented)
10. Schwarz, J. B.; Meyers, A. I. J. Org. Chem. 1998, 63, 1732.
11. Corey, E. J.; Ishihara, K. Tetrahedron Lett. 1992, 58, 6807.
12. We carried out solvent studies and found that THF, alkanes, and other relatively non-polar solvents had little effect on the rearrangements and the resulting diastereoselectivities. Except for providing wider temperature ranges, little else was observed. This is in agreement with the generally accepted non-polar nature of the rearrangements. No studies were carried out in highly polar solvents (e.g. alcohols, acids).