Cobalt-catalyzed alkenylation of zinc organometallics

Tetrahedron Letters

Volumn 39, Issue 34, 1998, Pages 6163-6166

  Avedissian, Hovsep ^a,b   Bérillon, Laurent ^a   Cahiez, Gérard ^b   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b Ecl Sup Chim Organique Minerale   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; ORGANOMETALLIC COMPOUND; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; FRANCE; STEREOCHEMISTRY;

EID: 0032552141     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01267-2     Document Type: Article

References (15)

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2. (b) King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc., Chem. Commun. 1977, 683.
3. (c) Negishi, E. Acc. Chem. Res. 1982, 15, 340.
4. 2. (a) Erdik, E. Tetrahedron 1992, 48, 9577.
5. (b) Quesnelle, C. A.; Familoni, O. B.; Snieckus, V. Synlett 1994, 349.
6. (c) Rossi, R.; Bellina, F.; Carpita, A.; Gori, R. Synlett 1995, 344.
7. (d) Abarbri, M.; Parrain, J. L.; Cintrat, J.-C.; Duchêne, A. Synthesis 1996, 82.
8. (e) Anderson, B. A.; Harn, N. K. Synthesis 1996, 583.
9. 3. (a) Marquais, S.; Arlt, M. Tetrahedron Lett. 1996, 37, 5491.
10. (b) Rottländer, M.; Knochel, P. Tetrahedron Lett. 1997, 38, 1749;
11. (c) Rottländer, M.; Knochel, P. Synlett 1997, 1084.
12. 4. (a) Devasagayaraj, A.; Knochel, P. Tetrahedron Lett. 1995, 36, 8411;
13. (b) Reddy, C. K.; Knochel, P. Angew. Chem. 1996, 108, 1812.
14. 5. Cahiez, G.; Avedissian, H. Tetrahedron Lett. preceeding paper.
15. 6. Typical procedure: Preparation of (E)-10-chloro-6-decenyl acetate (8d). A dry three-necked flask equipped with a magnetic stirring bar, a thermometer and a septum was charged with Co(acac)2 (320 mg, 1.3 mmol) in a 5:2 mixture of THF:NMP (7 mL) and heated to 50 °C. (E)-5-Chloro-1-iodo-1-pentene (3b) (1.15 g, 5 mmol) was added dropwise followed by 5-acetoxypentylzinc iodide (15 mmol prepared from 5-iodopentyl acetate (3.84 g, 15 mmol), zinc dust (3.9 g, 60 mmol) in THF (8 mL). The reaction mixture was stirred at 55 °C for 8 h and worked up as usually. The crude reaction oil obtained after evaporation of the solvents was purified by chromatography (hexane:ether 95:5) yielding pure unsaturated chloroester 8d (804 mg, 69 % yield).