Intramolecular Diels - Alder reaction of chiral silatrienes: Synthesis of 4a,7,8,8a-tetrahydro-4-silaisochroman-1-ones

European Journal of Organic Chemistry

Volumn , Issue 17, 2000, Pages 3039-3046

  Coelho, Paulo J ^a   Blanco, Luis ^a  

^a CNRS   (France)

Author keywords

Chirality; Cycloadditions; Intramolecular Diels Alder reaction; Silicon; Tetrahydro 4 silaisochroman 1 ones

Indexed keywords

(4 METHYL 1 OXO 4A,7,8,8A TETRAHYDRO 4 SILAISOCHROMAN 4 YL)METHYL PHENYLACETATE; 4A,7,8,8A TETRAHYDRO 4 SILAISOCHROMAN 1 ONE DERIVATIVE; ACRYLIC ACID; ACRYLIC ACID DERIVATIVE; ALUMINUM DERIVATIVE; ESTER; METHYL GROUP; SILICON; SILICON DERIVATIVE; UNCLASSIFIED DRUG; [(BUTA 1,3 DIENYL)METHYL(TRIISOPROPYLSILYLOXYMETHYL)SILYL]METHYL ACRYLATE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ESTERIFICATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033816662     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200009)2000:17<3039::AID-EJOC3039>3.0.CO;2-X     Document Type: Article

References (35)

1. R. J. P. Corriu, C. Guérin, J. J. E. Moreau, in Topics In Stereochemistry (Eds.: E. L. Eliel, S. H. Wilen, N. L. Allinger), John Wiley & Sons, New York, 1984, Vol. 15, p. 43-198.
2. [2a] H. Nishiyama, T. Kitajima, M. Matsumoto, K. Itoh, J. Org. Chem. 1984, 49, 2298-2300.
3. G. Stork, M. Kahn, J. Am. Chem. Soc. 1985, 107, 500-501.
4. G. Stork, M. J. Sofia, J. Am. Chem. Soc. 1986, 108, 6826-6828.
5. G. Stork, Bull. Chem. Soc. Jpn. 1988, 61, 149-154.
6. R. V. Bonnert, M. J. Davies, J. Howarth, P. R. Jenkins, J. Chem. Soc., Chem. Commun. 1990, 148-149.
7. K. Tamao, K. Maeda, T. Yamaguchi, Y. Ito, J. Am. Chem. Soc. 1989, 111, 4984-4985.
8. M. Koreeda, I. A. George, J. Am. Chem. Soc. 1986, 108, 8098-8100.
9. A. G. Myers, D. Y. Gin, K. L. Widdowson, J. Am. Chem. Soc. 1991, 113, 9661-9663.
10. [3a] S. Anwar, A. P. Davis, Tetrahedron 1988, 44, 3761-3770.
11. K. Tamao, T. Nakajima, R. Sumiya, H. Arai, N. Higuchi, Y. Ito, J. Am. Chem. Soc. 1986, 108, 6090-6093.
12. M. R. Hale, A. H. Hoveyda, J. Org. Chem. 1992, 57, 1643-1645.
13. S. Anwar, G. Bradley, A. P. Davis, J. Chem. Soc., Perkin Trans. 1 1991, 1383-1389.
14. K. Tamao, T. Tohma, N. Inui, O. Nakayama, Y. Ito, Tetrahedron Lett. 1990, 31, 7333-7336.
15. [4a] K. Nakanishi, K. Mizuno, Y. Otsuji, J. Chem. Soc., Chem. Commun. 1991, 90-92.
16. S. A. Fleming, S. C. Ward, Tetrahedron Lett. 1992, 33, 1013.
17. [5a] K. Tamao, K. Kobayashi, Y. Ito, J. Am. Chem. Soc. 1989, 111, 6478-6480.
18. J. W. Gillard, R. Fortin, E. L. Grimm, M. Maillard, M. Tjepkema, M. A. Bernstein, R. Glaser, Tetrahedron Lett. 1991, 32, 1145-1148.
19. D. Craig, J. C. Reader, Tetrahedron Lett. 1990, 31, 6585-6588.
20. D. Craig J. C. Reader. Tetrahedron Lett. 1992, 33, 4073-4076.
21. S. M. Sieburth, L. Fensterbank, J. Org. Chem. 1992, 57, 5279-5281.
22. G. Stork, T. Y. Chan, G. A. Breault, J. Am. Chem. Soc. 1992, 114, 7578-7579.
23. K. J. Shea, K. S. Zandi, A. J. Staab, R. Carr, Tetrahedron Lett. 1990, 31, 5885-5888.
24. K. J. Shea, A. J. Staab, K. S. Zandi, Tetrahedron Lett. 1991, 32, 2715-2718.
25. L. H. Sommer, C. L. Frye, J. Am. Chem. Soc. 1959, 81, 1013.
26. [7a] R. G. Daniels, L. A. Paquette. Organometallics 1982, 1, 1449-1453.
27. A. G. Brook, W. W. Limburg, J. Am. Chem. Soc. 1963, 85, 832-833.
28. A. G. Brook, J. D. Pascoe, J. Am. Chem. Soc. 1971, 93, 6224-6227.
29. [8a] A. Chapeaurouge, S. Bienz, Helv. Chim. Acta 1993, 76, 1876-1889.
30. S. Bienz, A. Chapeaurouge, Helv. Chim. Acta 1991, 74, 1477-1488.
31. [9a] A. Djerourou, L. Blanco, Tetrahedron Lett. 1991, 32, 6325-6326.
32. A. Djerourou, L. Blanco, Phosphorus, Sulfur and Silicon 1999, 149. 107.
33. The preparation of buta-1,3-dienylmagnesiurn chloride from a mixture of (E)-and (Z)-chlorobutadiene (E/Z = 3:7) has been reported (see T. Ishii, N. Kawamura, S. Matsubara, K. Utimoto, S. Kozima, T Hitomi, J. Org. Chem. 1987, 52, 4416-4418). Treatment of isobutyraldehyde with this reagent gave a mixture of dienyl alcohols with a 3:7 E/Z ratio. This would seem to have been a fortuitous stereospecific reaction as these dienyl alcohols with the same E/Z ratio (3:7) were obtained starting from a mixture of chlorobutadienes with E/Z = 6:94.
34. H. G. Viehe, Angew. Chem. Int. Ed. Engl. 1963, 75, 793-794.
35. Transesterifications of methyl acrylate, phenyl acetate and fumarate with 2-silapropanediol 4 proved to be too slow at -20 °C. When these reactions were performed at room temperature, the monoesters 6b-d were isolated in low yields (15-46%) and with very low ee (0-16%).