Carboxylates as pronucleophiles in the phosphine-catalyzed γ-addition reaction

Tetrahedron Letters

Volumn 40, Issue 48, 1999, Pages 8465-8467

  Alvarez Ibarra, Carlos ^a   Aurelio, G ^a   De La Oliva, Cristina Gómez ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Addition reaction; Carboxylic acid derivatives; Carboxylic acids; Phosphines; Sodium; Sodium compounds

Indexed keywords

ALKYNE DERIVATIVE; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; PHOSPHINE DERIVATIVE; SODIUM; SODIUM DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; ELECTRON; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0033607445     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01775-X     Document Type: Article

References (14)

1. Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 3167-3168.
2. Trost, B. M.; Dake, G. R. J. Org. Chem. 1994, 62, 5670-5671.
3. Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819-10820.
4. For reviews on conjugate additions, see: (a) Perlmutter, P. In Conjugate Addition Reactions in Organic Synthesis: Pergamon Press: Oxford, 1992; pp. 1-127.
5. (b) Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp. 1-67.
6. 3P, see: Inanaga, J.; Baba, Y.; Hanamoto, T. Chem. Lett. 1993, 241-244.
7. For previous synthesis of γ-hydroxy-α, β-unsaturated carbonyl compounds, see: (a) Suryawanshi, S. N.; Fuchs, P. L. Tetrahedron Lett. 1981, 22, 4201-4204.
8. (b) Reich, H. J.; Clark, M. C.; Willis Jr., W. W. J. Org. Chem. 1982, 47, 1618-1623.
9. (c) Nokami, J.; Nishimuri, A.; Sunami, M.; Wakabayashi, S. Tetrahedron Lett. 1987, 28, 644-650.
10. 2O solution.
11. 3P (0.1 mmol), the sodium carboxylate (2, 1.0 mmol) and the corresponding carboxylic acid (3, 1.0 mmol) in toluene (5 mL) was heated at 80°C for 24 h under Ar. Upon cooling, the mixture was filtered and the solid was washed with ether. The combined organic fractions were concentrated and the residue was purified by silica gel chromatography (hexane:ethyl acetate, 90:10).
12. 3, 300 MHz) spectra.
13. For synthetic uses of γ-hydroxy-α, β-unsaturated carbonyl compounds, see, for example: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 3543-3544;
14. (b) Nokami, J.; Nishimuri, A.; Sunami, M.; Wakabayashi, S. Tetrahedron Lett. 1987, 28,644-650, and references cited therein.