Asymmetric synthesis of a constituent of iris essential oil by homoenolate alkylation of a chiral bicyclic lactam

Journal of Organic Chemistry

Volumn 63, Issue 5, 1998, Pages 1732-1735

  Schwarz, Jacob B ^a   Meyers, A I ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000116562     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9719214     Document Type: Note

References (15)

1. Schwarz, J. B.; Meyers, A. I. Tetrahedron 1997, 53, 8795.
2. For reviews of the chemistry of bicyclic lactams, see: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503.
3. Meyers, A. I.; Brengel, G. P. J. Chem. Soc., Chem. Commun. 1997, 1.
4. Isolation: (a) Naves, Y. R. Helv. Chim. Acta 1949, 32, 1351.
5. (b) Naves, Y. R. Helv. Chim. Acta ibid. 1949, 32, 2171.
6. (c) Treibs, W. Chem. Ber. 1950, 83, 431.
7. Structure determination: (d) Garnero, J.; Joulain, D. Riv. Ital. E.P.P.O.S. 1981, 63, 141.
8. For an enantioselective synthesis of 1, see: Chapuis, C.; Brauchli, R.; Thommen, W. Helv. Chim. Acta 1993, 76, 535.
9. Eberle, M. K.; Kahle, G. G. Tetrahedron Lett. 1980, 21, 2303.
10. Lajoie, G.; Lepine, F.; Maziak, L.; Belleau, B. Tetrahedron Lett. 1983, 24, 3815.
11. For recent applications of chiral bicyclic thiolactams, see: Devine, P. N.; Meyers, A. I. J. Am. Chem. Soc. 1994, 116, 2633.
12. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399.
13. Meerwein, H. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 1080.
14. Tartrate ketals have previously been used to determine ee's of chiral cyclohexanones: Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernandez, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron 1993, 49, 965. The tartrate ketals from (+)-1 and (±)-1 were prepared by the method described in ref 1.
15. Utaka, M.; Watabu, H.; Takeda, A. J. Org Chem. 1987, 52, 4363.