Opening norbornadiene homo Diels-Alder adducts to bicyclic systems

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1477-1480

  Chen, Yan ^a   Snyder, John K ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031550818     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00134-2     Document Type: Article

References (22)

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3. (b) Brunner, H.; Prester, F. J. Organomet. Chem. 1991, 414, 401, and references therein.
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8. 4 Rigby, H. J. PhD Dissertation, Baylor University, 1985.
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11. 6 (a) Greco, A.; Carbonaro, A.; Dall'Asta, G. J. Org. Chem. 1970, 35, 271.
12. (b) Takahashi, A.; Inukai, T. JCS, Chem. Commun. 1970, 1473.
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15. (e) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513.
16. 7 Preparation of 5a: ref 6d. Preparation of 5b from NBD and 2-butyne (94%) used the catalyst of Duan etal: Duan, I.-F.; Cheng, C.-H.; Shaw, J.-S.; Cheng, S.-S.; Liou, K.-F. JCS, Chem. Commun. 1991, 1347.
17. 8 For similar electrophile-catalyzed rearrangements of deltacyclenes: Tenaglia, A.; Pardigon, O.; Buono, G. J. Org. Chem. 1996, 61, 1129, and ref. therein.
18. 9 The brendane/brexane mixture 2f/3d was ultimately separated by GC for characterization.
19. 10 Preparation of 1f from NBD and maleic anhydride (65%) followed Lautens procedure for the cycloaddition of NBD with N-phenylmaleimide: ref. 1.
20. 11 For a review of Baeyer-Villager conditions: Krow, G. R. Tetrahedron 1981, 37, 2697.
21. 12 (a) de Armas, P.; Francisco, C. G.; Suarez, E. J. Am. Chem. Soc. 1993, 115, 8865.
22. (b) Kim, H.; C. Ziani-Cherif; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 792.