Selective conjugate alkylation of alkyllithium nucleophiles to α, β, γ, δ-unsaturated aldehydes with functionalized Lewis acid receptors

Chemistry Letters

Volumn , Issue 5, 1998, Pages 403-404

  Ooi, Takashi ^a   Kondo, Yuichiro ^a   Kon i, Kana ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002906572     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.403     Document Type: Article

References (16)

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3. c) P. Perlmutter, "Conjugate Addition Reactions in Organic Synthesis"; Pergamon: Oxford, 1992.
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7. Prepared according to the Meyers's protocol: A. I. Meyers, K. Tomioka, and M. P. Fleming, J. Org. Chem., 43, 3788 (1978).
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11. d) S. Saito and H. Yamamoto, J. Org. Chem., 61, 2928 (1996).
12. For information on the interaction of Li-F: a) N. J. R. von Eikema Hommes and P. v. R. Schleyer, Angew. Chem. Int. Ed. Engl., 31, 755 (1992).
13. b) J. M. Saa, P. M. Deya, G. A. Suner, and A. Frontera, J. Am. Chem. Soc. 114, 9093 (1992). For details, see: T. Yamazaki and T. Kitazume, J. Synth. Org. Chem. Jpn., 54, 665 (1996).
14. b) J. M. Saa, P. M. Deya, G. A. Suner, and A. Frontera, J. Am. Chem. Soc. 114, 9093 (1992). For details, see: T. Yamazaki and T. Kitazume, J. Synth. Org. Chem. Jpn., 54, 665 (1996).
15. Electron withdrawing substituents directly attached to the phenoxy ring dramatically affect the Lewis acidity of aluminum. However, the influence of fluoro substituents introduced to the ortho-phenyl groups of fluorinated ATPH derivatives on the Lewis acidity seems to be negligible compared to the parent ATPH, since the increase of the Lewis acidity of fluorinated ATPH derivatives would cause the preferential 1,2-addition of BuLi to the dienals. See: a) K. N. Houk and R. W. Strozier, J. Am. Chem. Soc., 95, 4094 (1973).
16. b) B. Deschamps, Tetrahedron, 34, 2009 (1978).