One pot synthesis of mono- and spirocyclic α-phosphonato-α,β- unsaturated cycloenones

Tetrahedron Letters

Volumn 39, Issue 20, 1998, Pages 3205-3208

  Gil, Jun Mo ^a   Hah, Jung Hwan ^a   Park, Kwang Young ^a   Oh, Dong Young ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032516326     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00460-2     Document Type: Article

References (15)

1. 1. For general reviews, see : (a) Maryanoff, B.E.; Beitz, A. B. Chem. Rev., 1989, 89, 863.
2. (b) Wadsworth, W. S. Jr, Org. React. (N. Y.), 1977, 25, 73.
3. (c) Walker, B. J. Organophosphorous Reagents in Organic Synthesis; Cadogan, J. I. G. Ed.; Academic Press: New York, 1974 ; pp 155-206.
4. (d) Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, L.; Schreiber, S. L., Eds.; Pergamon Press: Oxford, 1991; Vol. 1,chapter 3.1, pp 755-782.
5. (e) Wadsworth, W. S., Emmons, W. D. J. Am. Chem. Soc., 1961, 83, 1733.
6. 2. For review on vinylphosphonates and their synthetic applications, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
7. 3. Piers, E.; Abeysekera, B.; Scheffer, J. R. Tetrahedron Lett. 1979, 3279.
8. 4. Gloer, K. B.; Calogeropoulou, T.; Jackson, J. A.; Wiemer, D. F. J. Org. Chem., 1990, 55, 2842.
9. 3) δ 198.17(d, J=5.18 Hz), 161.97(d, J=5.48 Hz), 130.98(d, J=180 Hz), 62.28(d, J=5.93 Hz), 48.20(d, J=6.83 Hz), 26.50, 26.02(d, J=15.68 Hz), 21.61, 16.25(d, J=6.23 Hz), 11.19.
10. 6. Savignac, P.; Mathey, F. Tetrahedron Lett. 1976, 2829.
11. 7. Grieco, P.A.; Pogonowski, C.S. J. Am. Chem. Soc. 1973, 95, 3071.
12. 8. An,Y-Z.; An, J. G.; Wiemer, D. F. J. Org. Chem., 1994, 59, 8197.
13. 3) δ 202.22(d, J=4.28 Hz), 156.63(d, J=8.18 Hz), 141.77(d, J=3.3 Hz), 62.50(dd, J=53.85, 6.6 Hz), 43.76(d, J=137 Hz), 28.94(d, J=2.4 Hz), 16.20(t, J=3.83 Hz), 10.16.
14. 3) δ 8.28(td, 1H, J=2.57, 10.55 Hz)) of the β-vinyl hydrogen.
15. 3) δ 202.45,201.74(d, J=6.38 Hz), 62.31(d, J=5.1 Hz), 43.57(d, J=10.95 Hz), 42.19(d, J=126.68 Hz), 33.71, 28.72(d, J=7.8 Hz), 28.49(d, J=16.8 Hz), 29.97, 22.95, 21.65, 15.99(d, J=6.15 Hz).