Addition of 2,3-dihydro-5-furanyllithium to diisopropyl squarate as a means for the rapid generation of structurally complex oxygen-containing tetraquinane networks

Tetrahedron

Volumn 52, Issue 9, 1996, Pages 3075-3094

  Paquette, Leo A ^a   Morwick, Tina M ^a   Negri, Joanna T ^a   Rogers, Robin D ^b  

^a OHIO STATE UNIVERSITY   (United States)

^b NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030063470     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01096-3     Document Type: Article

References (25)

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12. See, for example: (a) Paquette, L. A.; Oplinger, J. A. Tetrahedron 1989, 45, 107.
13. (b) Paquette, L. A.; Dullweber, U.; Cowgill, L. D. Tetrahedron Lett. 1993, 34, 8019 and relevant references cited therein.
14. 5
15. Thomas, B. E., IV; Evanseck, J. D.; Houk, K. N. J. Am. Chem. Soc. 1993, 115, 4165 and relevant references cited therein.
16. Still, W. C.; Steliou, K. private communication. Through use of the Grid Search function within MODEL, a multiconformer run was performed within each molecule incorporating the appropriately stereodisposed three rings. In each case, over 300 conformers were generated and minimized to ensure arrival at the global minimum energy conformer. The MMX software program was then used to optimize the lowest energy conformer in each instance.
17. 1,4-Additions to squarate esters have been reported: (a) Dehmlow, E. V.; Schell, H. G. Chem. Ber. 1980, 113, 1.
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21. Morwick, T. M.; Doyon, J. to be published.
22. The general e xperimental protocols followed in this study parallel those described in a recent report: Paquette, L. A.; Ezquerra, J.; He, W. J Org. Chem. 1995, 60, 1435.
23. Sheldrick, G. M., SHELX76, a system of computer programs for X-ray structure determination as locally modified, University of Cambridge, England (1976).
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