Highly efficient synthesis of alka-1,3-dien-2-yltitanium compounds from alka-2,3-dienyl carbonates. A new, practical synthesis of 1,3-dienes and 2-iodo-1,3-dienes

Tetrahedron Letters

Volumn 37, Issue 49, 1996, Pages 8865-8868

  Okamoto, Sentaro ^a   Sato, Hiroyoshi ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ORGANOIODINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030566865     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02126-0     Document Type: Article

References (23)

1. 1. (a) Kasatkin, A.; Nakagawa, T.; Okamoto. S.; Sato, F. J. Am. Chem. Soc. 1995,117, 3881-3882.
2. (b) Nakagawa, T.; Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 3207-3210.
3. (c) Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136-8137.
4. (d) Zubaidha, P. K.; Kasatkin, A.; Sato, F. J. Chem. Soc. Chem. Commun. 1996, 197-198.
5. (e) Gao, Y.; Harada, K.; Sato, F. ibid. 1996, 533-534.
6. (f) Urabe, H.; Takeda, T.; Sato, F. Tetrahedron Lett. 1996, 37, 1253-1256.
7. (g) Yamazaki, T.; Kasatkin, A.; Kawanaka, Y.; Sato, F. J. Org. Chem. 1996, 61, 2266-2267.
8. (h) Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208-2216 and references cited therein.
9. 1b as shown below: (figure presented)
10. 3. Preparation of 2-metallo-1,3-diene compounds and their reactions with electrophiles, see: Mg: (a) Kondo, K.; Dobashi, S.; Matsumoto, M. Chem. Lett. 1976, 1077-1080.
11. (b) Nunomoto, S.; Yamashita, Y. J. Org. Chem. 1979, 44, 4788-4791.
12. (c) Shea, K. J.; Pham, P. Q. Tetrahedron Lett. 1983, 24, 1003-1006 and ref. 3d. Zn, A1:
13. (d) Pornet, J.; Randrianoelina, B.; Miginiac, L. J. Organomet. Chem. 1979, 174, 15-26 and ref. 3b. Li:
14. (e) Wada, E.; Kanemasa, S.; Fujiwara, I.; Tsuge, O. Bull. Chem. Soc. Jpn. 1985, 58, 1942-1945.
15. (f) Brown, P. A.; Jenkins, P. R.; J. Chem. Soc. Perkin Trans, 1, 1986, 1129-1131.
16. (g) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162-4169.
17. Syntheses of α-allenyl boron compounds have been reported: (h) Soumdararajan, R.; Li, G.; Brown, H. C. Tetrahedron Lett. 1995, 36, 2441-2444.
18. (i) Zheng, B.; Srebnik, M. J. Org. Chem. 1995, 60, 486-487.
19. 4. The formation of the regioisomer 4 in the reaction with aldehydes can also be explained by assuming the presence of 2,3-dien-1-yltitanium compounds at equilibrium through metallotropic rearrangement from 3 and their reaction via a 6-membered transition state.
20. 5. The compounds 3 prepared here did not react with ketones such as acetophenone and 2-nonanone presumably due to steric reasons.
21. 6. Ratovelomanana, V.; Hammoud, A.; Linstrumelle, G. Tetrahedron Lett. 1987, 28, 1649-1650. Mitani, M.; Kobayashi, Y.; Koyama, K. J. Chem. Soc. Perkin Trans, 1, 1995, 653-655.
22. 6. Ratovelomanana, V.; Hammoud, A.; Linstrumelle, G. Tetrahedron Lett. 1987, 28, 1649-1650. Mitani, M.; Kobayashi, Y.; Koyama, K. J. Chem. Soc. Perkin Trans, 1, 1995, 653-655.
23. 2NH (1 mL) at room temperature for 2 ∼ 6 h to remove a by-product, 1,4-diiodo-2,3-dimethylbutane, which was produced by iodolysis of a titanacyclopentane compound derived from 1 and propene generated in situ.