Intramolecular ene reaction of a chiral bicyclic lactam

Journal of Organic Chemistry

Volumn 73, Issue 24, 2008, Pages 9792-9794

  Resek, James E ^a,b  

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

^b Ricerca Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLIC LACTAMS; CHEMICAL EQUATIONS; CHIRAL AUXILIARIES; ENE REACTIONS; SYNTHESIS OF; TRI CYCLES;

CHEMICAL REACTIONS;

SYNTHESIS (CHEMICAL);

BICYCLO COMPOUNDS, HETEROCYCLIC; CYCLIZATION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; INDICATORS AND REAGENTS; LACTAMS; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 58049208385     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801696r     Document Type: Article

References (21)

1. Dedicated to the memory of Professor Albert I. Meyers.
2. Reviews: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503.
3. (b) Meyers, A. I. Stereocontrolled Org. Synth. 1994, 145-175.
4. More recent work: (c) Meyers, A. I.; Downing, S. V.; Weiser, M. J. J. Org. Chem. 2001, 1413-1419.
5. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 55, 8931-8952.
6. (e) Lemieux, R. M.; Devine, P. N.; Mechelke, M. F.; Meyers, A. I. J. Org. Chem. 1999, 64, 3585-3591.
7. (f) Groaning, M. D.; Brengel, G. P.; Meyers, A. I. J. Org. Chem. 1998, 63, 5517-5522.
8. (g) Schwarz, J. B.; Meyers, A. I. J. Org. Chem. 1998, 63, 1619-1629.
9. (h) Fray, A. H.; Meyers, A. I. J. Org. Chem. 1996, 61, 3362-3374.
10. (i) Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7084-7085.
11. For a general ene reaction review, see: (a) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050.
12. Reviews focusing on intramolecular ene reactions: (b) Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476-486.
13. (c) Conia, J. M.; Le Perchec, P. Synthesis 1975, 1-19.
14. (d) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer Verlag: Berlin, 1984.
15. Brown, E.; Guilmet, E.; Touet, J. Tetrahedron 1973, 29, 2589-2596.
16. Hucklin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 1082-1087.
17. 1H NMR. The presence of the solvents does not affect the subsequent reaction, and they were not rigorously removed.
18. Resek, J. E.; Meyers, A. I. Tetrahedron Lett. 1995, 7051-7054.
19. Burgess, L. E.; Meyers, A. I. J. Org. Chem. 1992, 57, 1656.
20. See, for example: Lautens, M.; Ren, Y. J. Am. Chem. Soc. 1996, 118, 10668-10669, and references cited therein.
21. For related compounds: Bartmann, W.; Rupp, H.; Beck, G.; Knolle, J. German Patent DE2947493, 1981.