Allylbarium in Organic Synthesis: Unprecedented α-Selective and Stereospecific Allylation of Carbonyl Compounds

Journal of the American Chemical Society

Volumn 113, Issue 23, 1991, Pages 8955-8956

  Yanagisawa, Akira ^a   Habaue, Shigeki ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84992534721     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00023a058     Document Type: Article

References (22)

1. Reviews: (a) Ioffe, S. T.; Nesmeyanov, A. N. The Organic Compounds of Magnesium, Beryllium, Calcium, Strontium and Barium; North-Holland: Amsterdam, 1967.
2. Nützel, K. In Houben-Weyl: Methoden der Organischen Chemie; Müller, E., Eds.; Thieme Verlag: Stuttgart, 1973; Vol. 13/2a, p 529.
3. Gowenlock, B. G.; Lindsell, W. E. In Journal of Organometallic Chemistry Library 3, Organometallic Chemistry Reviews; Seyferth, D., Davies, A. G., Fischer, E. O., Normant, J. F., Reutov, O. A., Eds.; Elsevier: Amsterdam, 1977; p 1.
4. Lindsell, W. E. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 1, Chapter 4, p 223.
5. Wakefield, B. J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; Vol. 7, Chapter 44.
6. Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 5893.
7. Allylbarium has, as yet, been prepared only by transmetalation with diallylmercury4 or tetraallyltin5 in THF.
8. West, P.; Woodville, M. C. Ger. Offen. 2,132,955, 1972.
9. West, P.; Woodville, M. C. U.S. Pat. 3,766,281, 1973.
10. Anhydrous Bal2 was prepared by drying commercially available Ba-I2· 2H2O with a heat gun under reduced pressure (5 Torr).
11. Highly reactive calcium has been prepared by the lithium biphenylide reduction of CaBr2 or Cal2; see: Wu, T.-C.; Xiong, H.; Rieke, R. D. J. Org. Chem. 1990, 55, 5045.
12. α:γ ratios of the products obtained by the reaction of benzaldehyde with geranylmetals: M = Mg, α:γ = <1:99 (99% yield); M = Ca, α:γ = 8:92 (38% yield); M = Li, α:γ = 47:53 (36% yield); M = Ce, α:γ = 72:28 (52% yield); preliminary results by A. Yanagisawa, S. Habaue, and H. Yamamoto.
13. Recent approaches to a-selective allylation: (a) Yamamoto, Y.; Maruyama, K. J. Org. Chem. 1983, 48, 1564.
14. Yamamoto, Y.; Maeda, N.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1983, 742.
15. Clarembeau, M.; Krief, A. Tetrahedron Lett. 1984, 25, 3629.
16. Araki, S.; Hatano, M.; Ito, H.; Butsugan, Y. J. Organomet. Chem. 1987, 333, 329.
17. Araki, S.; Butsugan, Y. Chem. Lett. 1988, 457.
18. Iqbal, J.; Joseph, S. P. Tetrahedron Lett. 1989, 30, 2421.
19. Indirect methods using acylsilanes as electrophiles: (g) Wilson, S. R.; Hague, M. S.; Misra, R. N. Org. Chem. 1982, 47, 747.
20. Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198.
21. Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441.
22. Highly stereocontrolled a-selective allylation using allylceriums has been reported by Cohen, see: Guo, B.-S.; Doubleday, W.; Cohen, T. J. Am. Chem. Soc. 1987, 109, 4710.