The palladium catalyzed hydrostannation of 1-alkenylphosphonates: A new approach to stereodefined α,β-disubstituted vinylphosphonates

Synthetic Communications

Volumn 33, Issue 14, 2003, Pages 2511-2517

  Huang, Xian ^a,b   Xiong, Zheng Chang ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

1,1 Di functional reagent; 1 Alkenylphosphonates; Hydrostannation; Palladium catalyst

Indexed keywords

PALLADIUM; PHOSPHONIC ACID DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; STEREOSPECIFICITY; SYNTHESIS;

EID: 0042564669     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120021842     Document Type: Article

References (13)

1. (a) Mitchell, T.N.; Wickenkamp, R.; Amamria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868;
2. (b) Lipshutz, B.H.; Keil, R.; Barton, J.C. Tetrahedron Lett. 1992, 33, 5861;
3. (c) Huang, X.; Ma, Y. Synth. Commun. 1997, 27, 2407.
4. For a recent review, see: Minami, I.T.; Motoyoshiya, J. Selected recent reactions of vinylphosphonates include, aziridination. Synthesis 1992, 333; (a) Kim, D.Y.; Rhie, D.Y. Epoxidation. Tetrahedron 1997, 53, 13603; (b) Cristau, H.J.; Mbiana, X.Y.; Beziat, Y.; Gasc, M.B. Organocuprate addition. J. Organomet. Chem. 1998, 571, 189; (c) Afavinkia, K.; Binch, H.M.; Modi, C. Tetrahedron Lett. 1998, 39, 7419.
5. For a recent review, see: Minami, I.T.; Motoyoshiya, J. Selected recent reactions of vinylphosphonates include, aziridination. Synthesis 1992, 333; (a) Kim, D.Y.; Rhie, D.Y. Epoxidation. Tetrahedron 1997, 53, 13603; (b) Cristau, H.J.; Mbiana, X.Y.; Beziat, Y.; Gasc, M.B. Organocuprate addition. J. Organomet. Chem. 1998, 571, 189; (c) Afavinkia, K.; Binch, H.M.; Modi, C. Tetrahedron Lett. 1998, 39, 7419.
6. For a recent review, see: Minami, I.T.; Motoyoshiya, J. Selected recent reactions of vinylphosphonates include, aziridination. Synthesis 1992, 333; (a) Kim, D.Y.; Rhie, D.Y. Epoxidation. Tetrahedron 1997, 53, 13603; (b) Cristau, H.J.; Mbiana, X.Y.; Beziat, Y.; Gasc, M.B. Organocuprate addition. J. Organomet. Chem. 1998, 571, 189; (c) Afavinkia, K.; Binch, H.M.; Modi, C. Tetrahedron Lett. 1998, 39, 7419.
7. For a recent review, see: Minami, I.T.; Motoyoshiya, J. Selected recent reactions of vinylphosphonates include, aziridination. Synthesis 1992, 333; (a) Kim, D.Y.; Rhie, D.Y. Epoxidation. Tetrahedron 1997, 53, 13603; (b) Cristau, H.J.; Mbiana, X.Y.; Beziat, Y.; Gasc, M.B. Organocuprate addition. J. Organomet. Chem. 1998, 571, 189; (c) Afavinkia, K.; Binch, H.M.; Modi, C. Tetrahedron Lett. 1998, 39, 7419.
8. As intermediates in drugs or biological investigation compounds. (a) Harndn, M.R.; Parrat, M.J.; Perkin, R.M. J. Med. Chem. 1993, 36, 1343; (b) Magati, S.; Phadtare, S.; Zemlica, J. J. Org. Chem. 1992, 57, 2320.
9. As intermediates in drugs or biological investigation compounds. (a) Harndn, M.R.; Parrat, M.J.; Perkin, R.M. J. Med. Chem. 1993, 36, 1343; (b) Magati, S.; Phadtare, S.; Zemlica, J. J. Org. Chem. 1992, 57, 2320.
10. Pereyne, M.; Quintand, J.P.; Rahm, A. Tin in Organic Chemistry; Butterworth: London, 1980.
11. (a) Kenyon, G.L.; Westheimer, F.H. J. Am. Chem. Soc. 1966, 88, 3557;
12. (b) Benzra, C.; Nseic, S.; Qurisson, G. Bull. Soc. Chim. Fr. 1967, 1140.
13. Beringer, F.M.; Drexler, E.; Gindler, M.; Lumpkin, C.C. J. Am. Chem. Soc. 1953, 75, 2705.