Stereoselective manganese-catalyzed coupling reaction of conjugated chloroenynes and chlorodienes with Grignard reagents

Synlett

Volumn , Issue 3, 1998, Pages 325-327

  Alami, Mouâd ^a   Ramiandrasoa, Parfait ^a   Cahiez, Gérard ^a  

^a Allée du Réseau Jean Marie Buckmaster   (France)

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EID: 0007485735     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (15)

1. Organomanganese Reagents XXXVII. For part XXXVI see: Cahiez, G.; Razafinsalama, L.; Laboue, B.; Chau, F. Tetrahedron Lett., in press.
2. For reviews, see: a/ Cahiez, G. Manganese (II) Chloride in Encyclopedia of Reagents for Organic Synthesis, L. Paquette Ed., Wiley, Chichester 1995, 3227.
3. b/ Cahiez, G. Anales de Química 1995, 91, 561.
4. Cahiez, G.; Bernard, D.; Normant, J. J. Organomet. Chem. 1976, 113, 99.
5. Cahiez, G.; Bernard, D.; Normant, J. J. Organomet. Chem. 1976, 113, 107.
6. Symetrical 1,3-diene and diphenyl are also obtained.
7. Ramiandrasoa, P.; Bréhon, B.; Thivet, A.; Alami, M.; Cahiez, G. Tetrahedron Lett. 1997, 38, 2447.
8. For reviews, see: (a) Linstrumelle, G.; Alami, M. (E) and (Z)-dichloroethylene in Encyclopedia of Reagents for Organic Synthesis, Paquette, L.; Ed., Wiley, Chichester 1995, 3, 1710.
9. (b) Chemin, D.; Linstrumelle, G. Tetrahedron 1994, 50, 5335.
10. (c) Alami, M.; Gueugnot, S.; Domingues, E.; Linstrumelle, G. Tetrahedron 1995, 51, 1209.
11. 2•2LiCl see: Cahiez, G. Butyl Manganese Chloride and Related Reagents in Encyclopedia of Reagents for Organic Synthesis, L. Paquette Ed., Wiley, Chichester 1995, 925.
12. 3) δ 148.65, 107.50, 88.90, 79.25, 41.10, 32.35, 31.10, 28.55, 26.00, 25.80, 22.20, 19.30, 13.95.
13. Determined by capillary G.C. analysis, OV-1, 25 m x 0.33 mm, 0.5μm film thickness.
14. Isomerization of secondary or tertiary alkyl groups to primary alkyl groups is frequently observed in the coupling of sec- or tert-alkyl Grignard reagents with alkenyl halides catalyzed by Ni or Pd complexes, see: Hayashi, T.; Konishi, M.; Yokota, K.; Kumada, M. Chem. Lett. 1980, 767. see also ref. 12.
15. 2(dppf) is known to limit side reactions particularly β-elimination see: Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158.