Lewis Acid Catalyzed Diels-Alder Reactions of Highly Hindered Dienophiles

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 4143-4146

  Hubbard, Robert D ^a   Miller, Benjamin L ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001322795     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9801667     Document Type: Article

References (15)

1. For recent reviews of the Diels-Alder reaction, including Lewis acid catalysis, see: (a) Kobayashi, S. Synlett 1994, 689-701. (b) Kagan, H. B.; Riaut, O. Chem. Rev. 1992, 92, 1007-1019. (c) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876-889.
2. For recent reviews of the Diels-Alder reaction, including Lewis acid catalysis, see: (a) Kobayashi, S. Synlett 1994, 689-701. (b) Kagan, H. B.; Riaut, O. Chem. Rev. 1992, 92, 1007-1019. (c) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876-889.
3. For recent reviews of the Diels-Alder reaction, including Lewis acid catalysis, see: (a) Kobayashi, S. Synlett 1994, 689-701. (b) Kagan, H. B.; Riaut, O. Chem. Rev. 1992, 92, 1007-1019. (c) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876-889.
4. (a) Miesch, M.; Cotté, A.; Franck-Neumann, M. Tetrahedron Lett. 1993, 34, 8085-8086.
5. (b) Dauben, W. G.; Kowalczyk, B. A.; Lichtenthaler, F. W. J. Org. Chem. 1990, 55, 2391-2398.
6. (c) Williams, R. V.; Sung, C.-L.; Kurtz, H. A.; Harris, T. M. Tetrahedron Lett. 1988, 29, 19-20.
7. (a) Kitano, K.; Katagiri, N.; Kaneko, C. Chem. Lett. 1994, 1285-1288.
8. (b) Netherlands Patent 86-1541 860613.
9. Methyl bromoacetate and propyl bromoacetate are commercially available and were used without further purification. Compounds 5a and 5d were made according to the procedure of Bradley, J. C., Büchi, G. J. Org. Chem. 1976, 41, 699-700, and used without purificaiton.
10. Cyclohexanecarboxyaldehyde (7b) was purchased from Aldrich Chemical Co. and used without further purification. Cyclopentanecarboxyaldehyde (7a) was prepared according to the procedure of Olah, G.; Prakash, S.; Arvanaghi, M. Synthesis 1984, 228-230.
11. Nagoaka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888.
12. 3 is well-known to react with acidic hydrogens with loss of methane; for example, see: Davidson, N.; Brown, H. C. J. Am. Chem. Soc. 1942, 64, 316-324.
13. The major product was assigned as the endo diastereomer by analysis of a DQF-COSY spectrum.
14. Proulx, G.; Bergman, R. G. Organometallics 1996, 15, 684-692.
15. 3 as implemented in Macromodel 6.0 (Still, W. C., et al., Columbia University, 1997).