Titanium-catalyzed cascade carboalumination of 2-alkyl-substituted dienes and related trienes

Tetrahedron Letters

Volumn 37, Issue 22, 1996, Pages 3803-3806

  Kondakov, Denis Y ^a   Wang, Shan ^a   Negishi, Ei Ichi ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; STEREOCHEMISTRY;

EID: 0030011606     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00693-4     Document Type: Article

References (11)

1. Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404.
2. For a Ti-catalyzed monocarboalumination of mono-enes, see (a) Dzhemilev, U. M.; Ibragimov, A. G.; Vostrikova, O. S.; Tolstikov, G. A.; Zelenova, L. M. Izv. Akad. Nauk SSSR, Ser. Khim 1981, 361.
3. (b) Dzhemilev, U. M.; Ibragimov, A. G.; Vostrikova, O. S.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1985, 207.
4. Shaughnessy, K. H.; Waymouth, R. M. J. Am. Chem. 1995, 117, 5873.
5. 2 (Normant, J. F.; Alexakis, A. Synthesis 1981, 841).
6. 2- and 3-Allylmethylenecyclohexanes were prepared by the Wittig methylenation of 2-allylcyclohexanone (Howard, W. L.; Lorette, N. B. Org. Synth. Coll. Vol. 5, 1973, 25) and 3-allylcyclohexanone (Hosomi, A.; Sakurai, H. J. Am. Chem. Soc. 1977, 99, 1673).
7. 2- and 3-Allylmethylenecyclohexanes were prepared by the Wittig methylenation of 2-allylcyclohexanone (Howard, W. L.; Lorette, N. B. Org. Synth. Coll. Vol. 5, 1973, 25) and 3-allylcyclohexanone (Hosomi, A.; Sakurai, H. J. Am. Chem. Soc. 1977, 99, 1673).
8. (a) Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771.
9. (b) Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1996, 118, 1577.
10. 6 to these cases is currently under investigation.
11. 13C NMR chemical shift of C-7 (16.9 ppm) in 8 with those of the corresponding carbon atoms in endo- and exo-3-methylbicyclo[3.3.1]nonanes (16.0 and 24.9 ppm, respectively) reported in the literature (Whitesell, J. K. Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy; Chapman and Hall: New York, 1987).