Diels-Alder reaction of sugar-derived cyclic dienophiles with cyclopentadiene. Factors affecting the reactivity and stereoselectivity

Organic Letters

Volumn 2, Issue 8, 2000, Pages 1073-1076

  Pellegrinet, Silvina C ^a   Spanevello, Rolando A ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042905734     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005619k     Document Type: Article

References (18)

1. Fotiadu, F.; Archavlis, A.; Buono, G. Tetrahedron Lett. 1990, 31, 4863.
2. Collins, P.; Ferrier, R. Monosaccharides; John Wiley & Sons, Inc: New York, 1995.
3. Bols, M. Carbohydrate Building Blocks; John Wiley & Sons, Inc.: New York, 1996.
4. Cycloaddition Reactions in Carbohydrate; Chemistry; Giuliano, R. M. Ed.; ACS Symposium Series 494; American Chemical Society: Washington, DC, 1992.
5. Rehnberg, N.; Sundin, A.; Magnusson, G. J. Org. Chem. 1990, 55, 5477.
6. Kim, K. S.; Cho, I. H.; Joo, Y. H.; Yoo, I. Y.; Song, J. H.; Ko, J. H. Tetrahedron Lett. 1992, 33, 4029.
7. Spanevello, R. A.; Pellegrinet, S. C. Synth. Comm. 1995, 25, 3663.
8. 15-H showed the exo character of the addition.
9. Pellegrinet, S. C.; Spanevello, R. A. Tetrahedron: Asymmetry 1997, 8, 1983.
10. Pellegrinet, S. C.; Spanevello, R. A. Tetrahedron Lett. 1997, 38, 8623.
11. Rousch, W. R.; Brown, B. B. J. Org. Chem. 1992, 57, 3380.
12. Takeda, K.; Imaoka, I.; Yoshii, E. Tetrahedron 1994, 50, 10839.
13. All attempts to obtain these ketones directly from the aldehyde precursor, the nitrile 9 (Scheme 3) through a nucleophilic addition were fruitless.
14. The structure of the cycloadducts were assigned on the basis of the NOE experiments as described in ref 8 for cycloadduct 2.
15. 4 in methylene chloride at -78°C.
16. Sauer, J.; Wiest, H.; Mielert, A. Chem. Ber. 1964, 97, 3183.
17. The spectroscopic and physical properties of all new compounds reported herein are in complete agreement with the assigned structures.
18. Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779 and references cited therein.