Highly diastereoselective Diels-Alder reactions of Baylis-Hillman adducts

Organic Letters

Volumn 7, Issue 13, 2005, Pages 2555-2557

  Aggarwal, Varinder K ^a   Patin, Amaury ^a,b   Tisserand, Steve ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28644438137     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050584f     Document Type: Article

References (13)

1. Baylis, A. B.; Hillman, M. E. D. Offenlegungsschrift 2155113, 1972; U.S. Patent 3,743,669; Chem. Abstr. 1972, 77, 34174.
2. For reviews, see: (a) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049.
3. (b) Ciganek, E. Org. React. 1997, 51, 201.
4. (c) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
5. (d) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
6. Aggarwal, V. K.; Emme, I.; Fulford. S. J. Org. Chem. 2003, 68, 692.
7. Basavaiah, D.; Rao A. J.; Satyanarayana T. Chem Rev. 2003, 103, 811.
8. Palomo, C.; Oiarbide M.; Garcia, J. M.; Gonzalez, A.; Lecumberri, A.; Linden, A. J. Am. Chem. Soc. 2002, 124, 10288.
9. 4, or TFA, no Diels-Alder adducts were obtained.
10. Berson, J. A.; Hamlet, J.; Mueller, W. A. J. Am. Chem. Soc. 1962, 84, 297.
11. Roush W. R.; Brown B. B. J. Org. Chem. 1992, 57, 3380.
12. Cisoid or transoid conformation refers to the conformation around the σ-bond linking the alkene and the carbonyl group in the Baylis-Hillman dienophile.
13. Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808.