Anti-Carbometalation of Homopropargyl Alcohols and Their Higher Homologues via Non-Chelation-Controlled Syn-Carbometalation and Chelation-Controlled Isomerization

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 784-785

  Ma, Shengming ^a   Negishi, Ei Ichi ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000243839     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9622688     Document Type: Article

References (18)

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3. (b) Negishi, E.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639.
4. Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
5. (a) Normant, J. F.; Bourgain, M. Tetrahedron Lett. 1971, 2583.
6. (b) Normant, J. F. J. Organomet. Chem. Lib. 1976, 1, 219.
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13. Conversion of 6 to 8 was performed by Ms. F. Liu in our laboratories.
14. See, however: Kocienski, P.; Wadman, S.; Cooper, K. J. Am. Chem. Soc. 1989, 111, 2363.
15. Facile stereoisomerization of Si-substituted alkenylalanes and alkenyllithiums has been previously reported and discussed, (a) Miller, J. A.; Negishi, E. Israel J. Chem. 1984, 24, 76. (b) Negishi, E.; Takahashi, T. J. Am. Chem. Soc. 1986, 108, 3402.
16. Facile stereoisomerization of Si-substituted alkenylalanes and alkenyllithiums has been previously reported and discussed, (a) Miller, J. A.; Negishi, E. Israel J. Chem. 1984, 24, 76. (b) Negishi, E.; Takahashi, T. J. Am. Chem. Soc. 1986, 108, 3402.
17. Snider, B. B.; Karras, M. J. Organomet. Chem. 1979, 179, C37.
18. For a recent synthesis of (3Z,6E)-α-farnesene, which was 80% stereoselective, see: Ramaiah, P.; Pegram, J. J.; Millar, J. G. J. Org. Chem. 1995, 60, 6211.