The reaction of enaminones with grignard reagents: Synthesis of α,β- unsaturated ketones

Synthetic Communications

Volumn 28, Issue 10, 1998, Pages 1743-1753

  Fontenas, C ^a   Ait Haddou H ^a   Bejan, E ^a   Balavoine, G G A ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ENAMINE; KETONE DERIVATIVE; TOLUENE;

ALKYLATION; ARTICLE; COLUMN CHROMATOGRAPHY; POLYMERIZATION; SYNTHESIS;

EID: 2642679255     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808007005     Document Type: Article

References (17)

1. a) Perlmutter P., Conjugate Addition Reactions in Organic Synthesis; Pergamon; Oxford; 1992;
2. b) The Chemistry of Enones; ed. S. Patai Rappoport Z.; Willey, J.; Chichester 1989; vols. 1 and 2.
3. a) Birkofer L., Kim S.M. and Engels H.E., Chem. Ber , 1962, 95, 1495;
4. b) Ireland R.E. and Schiess P.W., J. Org. Chem., 1963, 28, 6;
5. c) Seebach D., Kolb M. and Gröbel B.T., Tetrahedron Lett., 1974, 3171;
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7. Fontenas C., Thèse de l'Université Paris-Sud; Orsay; France 1995.
8. Abdulla R.F. and Fuhr K.H., J. Org. Chem., 1978, 43, 4248.
9. Bartoli G., Cirmarelli C., Marcantoni E., Palmieri G. and Petrini M., J. Chem Soc, Chem. Commun., 1994, 715
10. a) Johnson W.S., J. Am. Chem. Soc., 1943, 65, 1317;
11. b) Jutz C., Ber., 1958, 97, 1867.
12. Preparation of 3-(2,2-dimethyl ethoxy) propylmagnesium chloride 3b: A 250ml two-necked flask was charged with 4.84g (200mmol) of magnesium in 20ml of anhydrous THF under an argon flow. To initiate the reaction 0.2ml of 1,2-dibromoethane was added. When the solvent was refluxing, a solution of 10g (66mmol) of 3-(2,2-dimethyl ethoxy) propylchloride and 2ml of 1,2-dibromoethane in 100ml of anhydrous THF were added over 1h. After additional stirring under reflux for 2h, the solution was used immediately.
13. Brederek H., Effenberger F., Botsh H., Rehn H., Chem. Ber., 1965, 98, 1081.
14. Bejan E., Aït-Haddou H., Daran J.C. and Balavoine G.G.A., Synthesis, 1996, 1012.
15. The Enaminone 7 was obtained in 4 steps as shown in the Scheme 2. (Formula Presented) Scheme 2 For the first step see: Wohl R.A., Synthesis, 1974, 38. For the second step see: Frimer A.R., Synthesis, 1977, 578. For the oxidation step see: Mancuso A.J., Swern D., Synthesis, 1981, 165. For transformation of the monoprotected diketone to the corresponding enaminone 7 see reef. 9.
16. The Enaminone 7 was obtained in 4 steps as shown in the Scheme 2. (Formula Presented) Scheme 2 For the first step see: Wohl R.A., Synthesis, 1974, 38. For the second step see: Frimer A.R., Synthesis, 1977, 578. For the oxidation step see: Mancuso A.J., Swern D., Synthesis, 1981, 165. For transformation of the monoprotected diketone to the corresponding enaminone 7 see reef. 9.
17. The Enaminone 7 was obtained in 4 steps as shown in the Scheme 2. (Formula Presented) Scheme 2 For the first step see: Wohl R.A., Synthesis, 1974, 38. For the second step see: Frimer A.R., Synthesis, 1977, 578. For the oxidation step see: Mancuso A.J., Swern D., Synthesis, 1981, 165. For transformation of the monoprotected diketone to the corresponding enaminone 7 see reef. 9.