Novel base-catalyzed olefination methodology. Stereoselective synthesis of (E)-α-benzenesulfinylvinylphosphonates

Synthesis

Volumn , Issue 1, 2000, Pages 99-102

  Shen, Yanchang ^a   Jiang, Guo Fang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Base catalyzed olefination; Benzenesulfinylvinylphosphonates; Stereoselective synthesis; Vinylphosphonates

Indexed keywords

ALKENE; BENZENE DERIVATIVE; BENZENESULFINYLVINYLPHOSPHONIC ACID; PHOSPHONIC ACID DERIVATIVE; SULFONIUM DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033968936     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6221     Document Type: Article

References (21)

1. For example, see: (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863 and references cited therein. Vedejs, E.; Marth, C. F.; Ruggeri, R. J. Am. Chem. Soc. 1988, 110, 3940. Vedejs, E.; Marth, C. F. J. Am. Chem. Soc. 1988, 110, 3948. Reitz, A. B.; Mutter, M. S.; Maryanoff, B. E. J. Am. Chem. Soc. 1984, 106, 1873. Burton, D. J.; Yang, Z. Y.; Qiu, W. Chem. Rev. 1996, 52, 1641.
2. For example, see: (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863 and references cited therein. Vedejs, E.; Marth, C. F.; Ruggeri, R. J. Am. Chem. Soc. 1988, 110, 3940. Vedejs, E.; Marth, C. F. J. Am. Chem. Soc. 1988, 110, 3948. Reitz, A. B.; Mutter, M. S.; Maryanoff, B. E. J. Am. Chem. Soc. 1984, 106, 1873. Burton, D. J.; Yang, Z. Y.; Qiu, W. Chem. Rev. 1996, 52, 1641.
3. For example, see: (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863 and references cited therein. Vedejs, E.; Marth, C. F.; Ruggeri, R. J. Am. Chem. Soc. 1988, 110, 3940. Vedejs, E.; Marth, C. F. J. Am. Chem. Soc. 1988, 110, 3948. Reitz, A. B.; Mutter, M. S.; Maryanoff, B. E. J. Am. Chem. Soc. 1984, 106, 1873. Burton, D. J.; Yang, Z. Y.; Qiu, W. Chem. Rev. 1996, 52, 1641.
4. For example, see: (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863 and references cited therein. Vedejs, E.; Marth, C. F.; Ruggeri, R. J. Am. Chem. Soc. 1988, 110, 3940. Vedejs, E.; Marth, C. F. J. Am. Chem. Soc. 1988, 110, 3948. Reitz, A. B.; Mutter, M. S.; Maryanoff, B. E. J. Am. Chem. Soc. 1984, 106, 1873. Burton, D. J.; Yang, Z. Y.; Qiu, W. Chem. Rev. 1996, 52, 1641.
5. For example, see: (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863 and references cited therein. Vedejs, E.; Marth, C. F.; Ruggeri, R. J. Am. Chem. Soc. 1988, 110, 3940. Vedejs, E.; Marth, C. F. J. Am. Chem. Soc. 1988, 110, 3948. Reitz, A. B.; Mutter, M. S.; Maryanoff, B. E. J. Am. Chem. Soc. 1984, 106, 1873. Burton, D. J.; Yang, Z. Y.; Qiu, W. Chem. Rev. 1996, 52, 1641.
6. Minami, T.; Motoyoshiya, J. Synthesis 1992, 333 and references cited therein.
7. Midura, W. H.; Mikolajczyk, M. Tetrahedron Lett. 1995, 36, 2871 and references cited therein.
8. Mikolajczyk, M. In Antibiotics and Antiviral Compounds - Chemical Synthesis and Modifications; Krohn, K.; Kirst, H.; Maag, H. Eds.; VCS: Weinheim, 1993; p 205.
9. Shen, Y. Acc. Chem. Res. 1998, 31, 584. Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. Shen, Y.; Li, P.; Ni, J. Sun, J. J. Org. Chem. 1998, 63, 9396.
10. Shen, Y. Acc. Chem. Res. 1998, 31, 584. Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. Shen, Y.; Li, P.; Ni, J. Sun, J. J. Org. Chem. 1998, 63, 9396.
11. Shen, Y. Acc. Chem. Res. 1998, 31, 584. Shen, Y.; Ni, J. J. Org. Chem. 1997, 62, 7260. Shen, Y.; Li, P.; Ni, J. Sun, J. J. Org. Chem. 1998, 63, 9396.
12. Zhou, Y.-G.; Li, A.-H.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1996, 1353. Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Chem. Commun. 1997, 1231. Li, A.-H.; Zhou, Y.-G.; Dai, L.-X.; Hou, X.-L.; Xia, L.-J.; Lin, L. J. Org. Chem. 1998, 63, 4338.
13. Zhou, Y.-G.; Li, A.-H.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1996, 1353. Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Chem. Commun. 1997, 1231. Li, A.-H.; Zhou, Y.-G.; Dai, L.-X.; Hou, X.-L.; Xia, L.-J.; Lin, L. J. Org. Chem. 1998, 63, 4338.
14. Zhou, Y.-G.; Li, A.-H.; Hou, X.-L.; Dai, L.-X. Chem. Commun. 1996, 1353. Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Chem. Commun. 1997, 1231. Li, A.-H.; Zhou, Y.-G.; Dai, L.-X.; Hou, X.-L.; Xia, L.-J.; Lin, L. J. Org. Chem. 1998, 63, 4338.
15. Zajac, W. W.; Walters, T. R.; Buzby, J.; Gagnon, J.; Labroli, M. Synth. Commun. 1994, 24, 427.
16. Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161. Murahashi, S.-I.; Naota,T.; Taki, H., Mizuno, M.;Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436.
17. Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161. Murahashi, S.-I.; Naota,T.; Taki, H., Mizuno, M.;Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436.
18. Kirilov, M.; Petrova, J. Chem. Ber. 1968, 101, 3467.
19. Nickson, T. E. J. Org. Chem. 1988, 53, 3870.
20. Gedye, R. N.; Westaway, K. C; Arora, P.; Bisson, R.; Khalil, A. H. Can. J. Chem. 1977, 55, 1218.
21. Drabowicz, J.; Lyzwa, P.; Popielarczyk, M.; Mikolajczyk, M. Synthesis 1990, 937.