Z-selective Horner-Wadsworth-Emmons reaction of (α-substituted ethyl (Diarylphosphono)acetates with aldehydes

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8411-8416

  Ando, Kaori ^a  

^a UNIVERSITY OF THE RYUKYUS   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0032514965     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981337a     Document Type: Article

References (23)

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2. Reviews of Horner-Wadsworth-Emmons reaction: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927. Boutagy, J.; Thomas, R. Chem. Rev. 1974, 74, 87-99.
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12. Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888. Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 259-260. Etemad-Moghadam, G.; Seyden-Penne, J. Tetrahedron 1984, 40, 5153-5166. Kinstle, T. H.; Mandanas, B. Y. J. Chem. Soc., Chem. Commun. 1968, 1699-1700.
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16. Highly Z-selective olefin formation was also reported in some cases: Rübsam, F.; Evers, A. M.; Michel, C.; Giannis, A. Tetrahedron 1997, 53, 1707-1714. Poss, M. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411-1414. Xiao, X.; Prestwich, G. D. Tetrahedron Lett. 1991, 32, 6843-6846.
17. Highly Z-selective olefin formation was also reported in some cases: Rübsam, F.; Evers, A. M.; Michel, C.; Giannis, A. Tetrahedron 1997, 53, 1707-1714. Poss, M. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411-1414. Xiao, X.; Prestwich, G. D. Tetrahedron Lett. 1991, 32, 6843-6846.
18. Highly Z-selective olefin formation was also reported in some cases: Rübsam, F.; Evers, A. M.; Michel, C.; Giannis, A. Tetrahedron 1997, 53, 1707-1714. Poss, M. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411-1414. Xiao, X.; Prestwich, G. D. Tetrahedron Lett. 1991, 32, 6843-6846.
19. 2(8-Ph-menthyl), highly E-selective olefin formation was reported: Kreuder, R.; Rein, T.; Reiser, O. Tetrahedron Lett. 1997, 38, 9035-9038.
20. 6
21. Kumamoto, T.; Koga, K. Chem. Pharm. Bull. 1997, 45, 753-755.
22. Ando, K. Unpublished results. A manuscript of a theoretical study of the HWE reaction is now in preparation.
23. For a free anion system, the rate-determining step was the ring closure of an oxyanion to an oxaphosphetane: Brandt, P.; Norrby, P.-O.; Martin, I.; Rein, T. J. Org. Chem. 1998, 63, 1280-1289.