Organoaluminum-promoted selective addition to fluorinated carbonyl compounds via pentacoordinate trialkylaluminum complexes

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7105-7108

  Ooi, Takashi ^a   Kagoshima, Naoko ^a   Uraguchi, Daisuke ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINUM DERIVATIVE; ORGANOFLUORINE DERIVATIVE;

ALKYLATION; ARTICLE; BINDING AFFINITY; CONFORMATIONAL TRANSITION; METAL BINDING; MOLECULAR INTERACTION; STRUCTURE ANALYSIS;

EID: 0032563839     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01508-1     Document Type: Article

References (20)

1. (1) (a) Welch, J. T.; Eswarakrishnan, S. "Fluorine in Bioorganic Chemistry"; John Wily & Sons: New York, 1991.
2. (b) Banks, R. E.; Smart, B. E.; Tatlow, J. C. "Organofluorine Chemistry: Principles and Commercial Applications"; Plenum Press: New York, 1994.
3. (c) Resnati, G. Tetrahedron 1993, 49, 9385.
4. (2) Welch, J. T. "Selective Fluorination in Organic and Bioorganic Chemistry"; American Chemical Society, 1991.
5. (3) Knunyants, I. L.; Yakobson, G. G. "Synthesis of Fluoroorganic Compounds"; Springer-Verlag: Berlin, 1985.
6. (4) Chambers, R. D. "Fluorine in Organic Chemistry"; Antony Rowe: Chippenham, 1973. See also ref 1b.
7. (5) Lide, D. R. "CRC Handbook of Chemistry and Physics"; 78th Edition, CRC Press: New York, 1997-1998.
8. (6) Ooi, T.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1997, 119, 5754. For the synthetic utility of forming Al-F bonds, see: (a) Posner, G. H.; Ellis, J. W.; Ponton, J. J. Fluorinr Chem. 1981, 19, 191.
9. (6) Ooi, T.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1997, 119, 5754. For the synthetic utility of forming Al-F bonds, see: (a) Posner, G. H.; Ellis, J. W.; Ponton, J. J. Fluorinr Chem. 1981, 19, 191.
10. (b) Posner, G. H.; Haines, S. R. Tetrahedron Lett. 1985, 26, 1823.
11. (c) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. Tetrahedron Lett. 1997, 38, 5679.
12. 4 can be utilized in ether solvent at 0-25 °C because of their solubility problem in toluene.
13. (8) General references: (a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
14. (b) Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem. Int. Ed. Engl. 1985, 24, 1.
15. (c) Braun, M. Angew. Chem. Int. Ed. Engl. 1987, 26, 24.
16. (d) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 317. See also ref 10.
17. (9) For a recent example, see: Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527 and references cited therein.
18. 1H NMR spectroscopy according to the aldol stereostructural assignment described by Heathcock. See: Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 2.
19. 3SiOTf was used. See: Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 37, 3899.
20. (12) The similar downfield effect is observed in several metal complexes of fluorinated macrocycles: Plenio, H.; Diodone, R. J. Am. Chem. Soc. 1996, 118, 356.