Diels-Alder reactivity of a ketovinylphosphonate with cyclopentadiene and furan

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2149-2152

  McClure, Cynthia K ^a   Hansen, Karl B ^b  

^a MONTANA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029945591     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00235-3     Document Type: Article

References (16)

1. Recipient of a NSF Career Advancement Award, 1994-96.
2. Results taken from the Undergraduate Degree with Distinction thesis of KBH at the University of Delaware.
3. Daniewski, W. M. and Griffin, C. E. J. Org. Chem. 1966, 31, 3236.
4. Buono, G. and Maffei, M. New J. Chem. 1988, 12, 923. Buono, G. and Maffei, M. Phos., Sulf., Silicon, Rel. Elem., 1993, 79, 297.
5. Buono, G. and Maffei, M. New J. Chem. 1988, 12, 923. Buono, G. and Maffei, M. Phos., Sulf., Silicon, Rel. Elem., 1993, 79, 297.
6. Zbiral, E.; Ohler, E.; Haslinger, E. Chem. Ber. 1982, 47, 1413.
7. Potter, B.V.L. Nat. Prod. Rep. 1990, 1. Reitz, A. B., Inositol Phosphates and Derivatives, American Chemical Society Symposium Series 463, American Chemical Society, Washington, D. C., 1991.
8. Potter, B.V.L. Nat. Prod. Rep. 1990, 1. Reitz, A. B., Inositol Phosphates and Derivatives, American Chemical Society Symposium Series 463, American Chemical Society, Washington, D. C., 1991.
9. McClure, C. K. and Grote, C. W., Tetrahedron Lett. 1991, 32, 5313.
10. 3 precipitated out of solution at temperatures lower than 0°C.
11. P-C = 3.8 Hz).
12. Fleming, I. Frontier Molecular Orbitals and Organic Chemical Reactions, Wiley, New York, 1976. Traven, V. F. Frontier Orbitals and Properties of Organic Molecules, Ellis Harwood, New York, 1992.
13. Fleming, I. Frontier Molecular Orbitals and Organic Chemical Reactions, Wiley, New York, 1976. Traven, V. F. Frontier Orbitals and Properties of Organic Molecules, Ellis Harwood, New York, 1992.
14. The program GAMESS was used in this calculation. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347.
15. 3. Kieselev, V. D.; Khuzyasheva, D. G.; Shakirov, I. M.; Konovalov, A. I. Zhur. Org. Khimii 1983, 19, 1789 (Eng. trans.).
16. The structures of 9 and 10 were consistent with all spectroscopic data.