Chemistry of 3,4-epoxy-2-methylene oxolanes: Highly diastereoselective electrophilic additions

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2777-2780

  Dalla, V ^a,b   Pale, P ^a,c  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b UNIV LILLE   (France)

^c UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAHYDROFURAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029915916     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00441-8     Document Type: Article

References (14)

1. Pale, P.; Chuche, J. Tetrahedron Lett. 1987, 28, 6447-6448.
2. Pale, P.; Chuche, J. Tetrahedron 1996, submitted.
3. Dalla, V.; Pale, P. Tetrahedron Lett. 1994, 35, 3525-3528.
4. P. Pale, J. Chuche Tetrahedron Lett. 1988, 29, 2947-2948.
5. Pale, P.; Bouquant, J.; Chuche, J.; Carrupt, P. A.; Vogel, P. Tetrahedron 1994, 50, 8035-8052.
6. Block, E.; Schwan, A. L. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford; 1991, vol. 4, p 329-362. Harding, K. E.; Tiner, T. H. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford; 1991, vol. 4, p 363-421. De la Mare, P. B. D.; Bolton, R. Electrophilic Additions to Unsaturated Systems, 2nd Ed.; Elsevier: Oxford, 1982.
7. Block, E.; Schwan, A. L. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford; 1991, vol. 4, p 329-362. Harding, K. E.; Tiner, T. H. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford; 1991, vol. 4, p 363-421. De la Mare, P. B. D.; Bolton, R. Electrophilic Additions to Unsaturated Systems, 2nd Ed.; Elsevier: Oxford, 1982.
8. Block, E.; Schwan, A. L. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford; 1991, vol. 4, p 329-362. Harding, K. E.; Tiner, T. H. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds; Pergamon: Oxford; 1991, vol. 4, p 363-421. De la Mare, P. B. D.; Bolton, R. Electrophilic Additions to Unsaturated Systems, 2nd Ed.; Elsevier: Oxford, 1982.
9. Toshima, K.; Tatsuda, K. Chem. Rev. 1993, 93, 1503-1531.
10. nOe as well as lanthanide-induced shift NMR experiments were used to established the relative stereochemistry of the adducts. These results will be disclosed in full account later.
11. Chrétien, J. R.; Coudert, J. D.; Ruasse, M. F. J. Org. Chem. 1993, 58, 1917-1921.
12. 14 works have shown that electrophilic additions of bromine reagents to unsymmetrically subtituted alkenes involve a highly dissymmetric cyclic bromonium species.
13. Chamberlin, R. A.; Mulholland, R. L.; Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 672-677.
14. Galland, B.; Evleth, E. M.; Ruasse, M. F. J. Chem. Soc., Chem. Commun. 1990, 898-900.