Enhancement in facial selectivity of a plane nonsymmetric double bond induced by a conjugating methoxycarbonyl group

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 517-520

  Gandolfi, Remo ^a   Amade, Mirko Sarzi ^a   Rastelli, Augusto ^b   Bagatti, Marisa ^b   Montanari, Dino ^b  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[2.2.2]OCTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030050190     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02176-0     Document Type: Article

References (18)

1. (a) Mander, L. N. Stereoselective Synthesis, ch. 12 in Eliel, E. E.; Wilen, S. H. Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994.
2. (b) Paquette, L. A.; Branan, B. M.; Rogers, R. D.; Bond, A. H.; Lange, H.; Gleiter, R. J. Am. Chem. Soc., 1995, 117, 5992-6001 and references therein,
3. (c) Wipf, P.; Kim, Y. J. Am. Chem. Soc., 1994, 116, 11678-11688.
4. (a) Raimondi, L.; Wu, Y.-D.; Brown, F. K.; Houk, K. N. Tetrahedron Lett., 1992, 33, 4405-4408.
5. (b)Annunziata, R.; Cinquini, M;; Cozzi, F.; Raimondi, L. Gazz. Chim. Ital., 1989, 119, 253-269.
6. (a) Farina, F.; Martin, M. V.; Sanchez, F. Heterocycles, 1986, 24, 2587-2592.
7. (b) de Lange, B.; Feringa, B. L. Tetrahedron Lett., 1988, 29, 5317-5320.
8. (a) Burdisso, M.; Gamba, A.; Gandolfi, R.; Toma, L.; Rastelli, A.; Schiatti, E. J. Org. Chem. 1990, 55, 3311-3321.
9. (b) Gandolfi, R.; Tonoletti, G.; Rastelli, A.; Bagatti, M. J. Org. Chem. 1993, 58, 6038-6048
10. 3 at -50°C in the case of 1b and 1e. These observations are consistent with the presence of one invertomer and, in the case 1b and 1e, of two rotamers about the amidic CON bond.
11. Compound 1f was the only detected product in the reaction of 2-methoxycarbonyl-1,3-cyclohexadiene with PhNO in contrast to the fact that 1e was formed as the minor product (rel.yield: 25%) in the reaction of the same diene with PhCONO : Boger, D. L.; Patel, P.; Takusagawa, F. J. Org. Chem., 1985, 50, 1911-1916.
12. 4a
13. 13C NMR and heterocorrelated spectra. Only exo adducts were isolated from the reactions of 4 because endo TSs experience insurmountable steric strains.
14. We thank the referee for stressing this point.
15. Houk, K. N.; Rondan, N. G.; Brown, F. K. Isr. J. Chem., 1983, 23, 3-9.
16. Rastelli, A.; Bagatti, M.; Gandolfi, R. J. Am. Chem Soc., 1995, 117, 4965-4975 and references therein.
17. This is not usually done, see Kahn, S. D.; Pau, C. F.; Chamberlin, A. R.; Hehre, W. J. J. Am. Chem. Soc., 1987, 109, 650-666 and Boger, D. L.; Patel, P. Tetrahedron Lett., 1986, 27, 683-686.
18. This is not usually done, see Kahn, S. D.; Pau, C. F.; Chamberlin, A. R.; Hehre, W. J. J. Am. Chem. Soc., 1987, 109, 650-666 and Boger, D. L.; Patel, P. Tetrahedron Lett., 1986, 27, 683-686.