Intermolecular carbolithiation of silylated enynes

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6689-6692

  Lorthiois, Edwige ^a   Marek, Ilane ^a   Meyer, Christophe ^a   Normant, Jean F ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ALLENE DERIVATIVE; ORGANOSILICON DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030576961     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01447-5     Document Type: Article

References (22)

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5. 2. a) Cherkasov, L.N. ; Bal'yan, K.V. ; Kormer, V.A. Zh.Org. Khim. 1968, 4, 204-207 Chem. Abstr. 1968, 68, 104634 e
6. 2. a) Cherkasov, L.N. ; Bal'yan, K.V. ; Kormer, V.A. Zh.Org. Khim. 1968, 4, 204-207 Chem. Abstr. 1968, 68, 104634 e
7. b) Kormer, V.A. ; Petrov, A.A. Zhur. Obshch. Kim. 1960, 30, 216-219 Chem. Abstr. 1960, 54, 22313 a
8. b) Kormer, V.A. ; Petrov, A.A. Zhur. Obshch. Kim. 1960, 30, 216-219 Chem. Abstr. 1960, 54, 22313 a
9. c) Id, 1960, 30, 3845-3848 Chem. Abstr.1961, 55, 20923
10. c) Id, 1960, 30, 3845-3848 Chem. Abstr.1961, 55, 20923
11. d) Miginiac, L. J. Organomet. Chem. 1982, 238, 235-266
12. 3. a) Meyer, C. ; Marek, I. ; Courtemanche, G. ; Normant, J.F. J. Org. Chem. 1995, 60, 863-871
13. b) Lorthiois, E. ; Marek, I. ; Meyer, C. ; Normant, J.F. Tetrahedron Lett. 1995, 36, 1263-1266
14. 4. A similar result was obtained in the allylmagnesiation of (E)-1-(trimethylsilyl)-but-1-en-3-o1. Kocienski, P. ; Love, C. ; Roberts, D.A. Tetrahedron Lett. 1989, 30, 6753-6756.
15. 5. Creary, X. J. Am. Chem. Soc. 1977, 99, 7632-7639
16. 6. The syn stereochemistry of the homopropargylic alcohol was deduced from the initial Zweifel's work a) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4567 and recently rewieved see ref. 7
17. b) Brasseur, D. ; Marek, I. ; Normant, J.F. Tetrahedron 1996, 52, 7235-7250
18. 7. Yamamoto, H. Comprehensive organic synthesis Trost, B.; Fleming, I., Eds Pergamon Press, New York, 1991, Vol 4, 81-98
19. 2U
20. 9. The same reaction on the E isomer does not lead to the carbometalated product.
21. 10. The corresponding allenic system is obtained as a 1:1 mixture of diastereomer
22. 11. Felkin, H. ; Swierczewski, G. ; Tambuté, A. Tetrahedron Lett. 1969, 707-710. In fact this study concerns the n-BuLi, TMEDA addition to secondary allylic alcohols having a E double bond.