Evaluation of several fluorinated ATPH derivatives as functionalized Lewis acid receptors for conjugate alkylation to α,β-unsaturated aldehydes with alkyllithium nucleophiles

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3951-3954

  Ooi, Takashi ^a   Kondo, Yuichiro ^a   Miura, Tomoya ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALUMINUM DERIVATIVE; ALUMINUM TRIS(2,6 DIPHENYLPHENOXIDE); LITHIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; SYNTHESIS;

EID: 0030914746     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00787-9     Document Type: Article

References (27)

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15. (e) Ooi, T.; Takahashi, M.; Maruoka, K. ibid. 1996, 118, 11307. See also: Ooi, T.; Maruoka, K. J. Synth. Org. Chem. Jpn. 1996, 54, 200.
16. (e) Ooi, T.; Takahashi, M.; Maruoka, K. ibid. 1996, 118, 11307. See also: Ooi, T.; Maruoka, K. J. Synth. Org. Chem. Jpn. 1996, 54, 200.
17. Ooi, T.; Kondo, Y.; Maruoka, K. Angew. Chem. Int. Ed. Engl., in press.
18. Reviews of conjugate alkylations: (a) Bergman, E. D.; Ginsburg, D.; Pappo, R. Org. React. 1959, 10, 179.
19. (b) House, H. O. Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; p 595.
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22. The interaction of Li-F: (a) von Eikema Hommes, N. J. R.; Schleyer, P. v. R. Angew. Chem. Int. Ed. Engl. 1992, 31, 755.
23. (b) Saa, J. M.; Deya, P. M.; Suner, G. A.; Frontera, A. J. Am. Chem. Soc. 1992, 114, 9093. For details, see: Yamazaki, T.; Kitazume, T. J. Synth. Org. Chem. Jpn. 1996, 54, 665.
24. (b) Saa, J. M.; Deya, P. M.; Suner, G. A.; Frontera, A. J. Am. Chem. Soc. 1992, 114, 9093. For details, see: Yamazaki, T.; Kitazume, T. J. Synth. Org. Chem. Jpn. 1996, 54, 665.
25. Unrau, C. M.; Campbell, M. G.; Sniekus, V. Tetrahedron Lett. 1992, 33, 2773.
26. The influence of fluoro substituents of fluorinated ATPH derivatives on the Lewis acidity seems to be negligible, since the increase of the Lewis acidity of fluorinated ATPH derivatives would cause the preferential 1,2-addition of BuLi to cinnamaldehyde. See: (a) Houk, K. N.; Strozier, R. W. J. Am. Chem. Soc. 1973, 95, 4094.
27. (b) Deschamps, B. Tetrahedron 1978, 34, 2009.