Manganese-catalyzed reaction of gem-dibrornoalkanes with Grignard reagents. Selective synthesis of alkenylsilanes

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3275-3278

  Kakiya, Hirotada ^a   Inoue, Rie ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030969334     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00601-1     Document Type: Article

References (14)

1. Inoue, R.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 5377-5380; Corey, E. J.; Posner, G. H. Tetrahedron Lett. 1970, 315-318; Kauffmann, T. Angew. Chem. Int. Ed. Engl. 1996, 35, 386-403.
2. Inoue, R.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 5377-5380; Corey, E. J.; Posner, G. H. Tetrahedron Lett. 1970, 315-318; Kauffmann, T. Angew. Chem. Int. Ed. Engl. 1996, 35, 386-403.
3. Inoue, R.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1996, 37, 5377-5380; Corey, E. J.; Posner, G. H. Tetrahedron Lett. 1970, 315-318; Kauffmann, T. Angew. Chem. Int. Ed. Engl. 1996, 35, 386-403.
4. Normant, J,-F.; Cahiez, G. "Organomanganous Reagents" in Modern Synthetic Methods, Vol. 3, pp. 173-216,1983, Scheffold, R. Ed., Otto Salle Verlag GmbH & Co,. Frankfurt am Main.
5. The reaction of 1,1-dibromoalkanes with trialkylzincate has been reported. Harada, T.; Kotani, Y.; Katsuhira.T.; Oku, A. Tetrahedron Lett. 1991, 32, 1573-1576.
6. Preparation of alkenylsilane: Colvin, E. W. Silicon in Organic Synthesis, pp. 44-82, 1981, Butterworth and Co Ltd, London; Weber, W. P. Silicon Reagents for Organic Synthesis, pp. 79-113, 1983, Springer-Verlag, Berlin.
7. Preparation of alkenylsilane: Colvin, E. W. Silicon in Organic Synthesis, pp. 44-82, 1981, Butterworth and Co Ltd, London; Weber, W. P. Silicon Reagents for Organic Synthesis, pp. 79-113, 1983, Springer-Verlag, Berlin.
8. 3SiCH(Br)MnBr2 regenerates 6. Oxidative insertion of manganese into organic halides has been reported. Hiyama, T.; Obayashi, M; Nakamura, A. Organometallics 1982, 1, 1249-1251; Kim, S.-H.; Hansen, M. V.; Rieke, R. D. Tetrahedron Lett. 1996, 37, 2197-2200; Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009-7012; Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37. 7049-7052.
9. 3SiCH(Br)MnBr2 regenerates 6. Oxidative insertion of manganese into organic halides has been reported. Hiyama, T.; Obayashi, M; Nakamura, A. Organometallics 1982, 1, 1249-1251; Kim, S.-H.; Hansen, M. V.; Rieke, R. D. Tetrahedron Lett. 1996, 37, 2197-2200; Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009-7012; Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37. 7049-7052.
10. 3SiCH(Br)MnBr2 regenerates 6. Oxidative insertion of manganese into organic halides has been reported. Hiyama, T.; Obayashi, M; Nakamura, A. Organometallics 1982, 1, 1249-1251; Kim, S.-H.; Hansen, M. V.; Rieke, R. D. Tetrahedron Lett. 1996, 37, 2197-2200; Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009-7012; Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37. 7049-7052.
11. 3SiCH(Br)MnBr2 regenerates 6. Oxidative insertion of manganese into organic halides has been reported. Hiyama, T.; Obayashi, M; Nakamura, A. Organometallics 1982, 1, 1249-1251; Kim, S.-H.; Hansen, M. V.; Rieke, R. D. Tetrahedron Lett. 1996, 37, 2197-2200; Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 7009-7012; Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37. 7049-7052.
12. Decomposition of the dialkylmanganese species has been reported to proceed by α,β-elimination of an hydrido-manganese species. Tamura, H.; Kochi, J. J. Organomet. Chem. 1971, 29, 111-129. They mentioned that secondary alkyl manganese has decomposed much more easily than primary one.
13. Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron, 1996, 52, 503-513.
14. 2-t-Bu instead of elimination of the Mn-H unit.