Synthesis of allyltitanium compounds by intramolecular nucleophilic acyl substitution reaction of alka-3,5-dienyl carbonates and their unusual regioselectivity in reaction with aldehydes

Chemical Communications

Volumn , Issue 2, 1996, Pages 197-198

  Zubaidha, P K ^a   Kasatkin, Aleksandr ^a,b   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002863145     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000197     Document Type: Article

References (16)

1. A. Kasatkin, T. Nakagawa, S. Okamoto and F. Sato, J. Am. Chem. Soc., 1995, 117, 3881; O. G. Kulinkovich, S. V. Sviridov, D. A. Vasilevskii and T. S. Pritytskaya, Zh. Org. Khim., 1989, 25, 2244; O. G. Kulinkovich, S. V. Sviridov and D. A. Vasilevskii, Synthesis, 1991, 234; E. J. Corey, A. Roa and M. C. Noe, J. Am. Chem. Soc., 1994, 116, 9345.
2. A. Kasatkin, T. Nakagawa, S. Okamoto and F. Sato, J. Am. Chem. Soc., 1995, 117, 3881; O. G. Kulinkovich, S. V. Sviridov, D. A. Vasilevskii and T. S. Pritytskaya, Zh. Org. Khim., 1989, 25, 2244; O. G. Kulinkovich, S. V. Sviridov and D. A. Vasilevskii, Synthesis, 1991, 234; E. J. Corey, A. Roa and M. C. Noe, J. Am. Chem. Soc., 1994, 116, 9345.
3. A. Kasatkin, T. Nakagawa, S. Okamoto and F. Sato, J. Am. Chem. Soc., 1995, 117, 3881; O. G. Kulinkovich, S. V. Sviridov, D. A. Vasilevskii and T. S. Pritytskaya, Zh. Org. Khim., 1989, 25, 2244; O. G. Kulinkovich, S. V. Sviridov and D. A. Vasilevskii, Synthesis, 1991, 234; E. J. Corey, A. Roa and M. C. Noe, J. Am. Chem. Soc., 1994, 116, 9345.
4. A. Kasatkin, T. Nakagawa, S. Okamoto and F. Sato, J. Am. Chem. Soc., 1995, 117, 3881; O. G. Kulinkovich, S. V. Sviridov, D. A. Vasilevskii and T. S. Pritytskaya, Zh. Org. Khim., 1989, 25, 2244; O. G. Kulinkovich, S. V. Sviridov and D. A. Vasilevskii, Synthesis, 1991, 234; E. J. Corey, A. Roa and M. C. Noe, J. Am. Chem. Soc., 1994, 116, 9345.
5. A. Kasatkin, S. Okamoto and F. Sato, Tetrahedron Lett., 1995, 36, 6075; see also: A. Kasatkin and F. Sato, Tetrahedron Lett., 1995, 36, 6079.
6. A. Kasatkin, S. Okamoto and F. Sato, Tetrahedron Lett., 1995, 36, 6075; see also: A. Kasatkin and F. Sato, Tetrahedron Lett., 1995, 36, 6079.
7. 2 and allylmagnesium compounds was reported, see: K. Asami, H. Yasuda and A. Nakamura, 47th National Meeting, Chemical Society Japan, Kyoto, 1982, Abstr. 4G25.
8. Concerning the intermolecular reaction of zirconium diene complexes with esters, see: Y. Kai, N. Kanehisa, K. Miki, N. Kasai, M. Akita, H. Yasuda and A. Nakamura, Bull. Chem. Soc. Jpn., 1983, 56, 3735.
9. Analogous coupling reactions with zirconium diene complexes are known, see: H. Yasuda, K. Tatsumi and A. Nakamura, Acc. Chem. Res., 1985, 18, 120.
10. M. T. Reetz, Organotitanium Reagents in Organic Synthesis, Springer Verlag, Berlin, 1986; L. Widler and D. Seebach, Helv. Chim. Acta, 1982, 65, 1085; F. Sato, S. Iijima and M. Sato, Tetrahedron Lett., 1981, 22, 243.
11. M. T. Reetz, Organotitanium Reagents in Organic Synthesis, Springer Verlag, Berlin, 1986; L. Widler and D. Seebach, Helv. Chim. Acta, 1982, 65, 1085; F. Sato, S. Iijima and M. Sato, Tetrahedron Lett., 1981, 22, 243.
12. M. T. Reetz, Organotitanium Reagents in Organic Synthesis, Springer Verlag, Berlin, 1986; L. Widler and D. Seebach, Helv. Chim. Acta, 1982, 65, 1085; F. Sato, S. Iijima and M. Sato, Tetrahedron Lett., 1981, 22, 243.
13. R. Hanko and D. Hoppe, Angew. Chem., Int. Ed. Engl., 1982, 21, 372; B. Wiedmann and D. Seebach, Angew. Chem., Int. Ed. Engl., 1983, 22, 31.
14. R. Hanko and D. Hoppe, Angew. Chem., Int. Ed. Engl., 1982, 21, 372; B. Wiedmann and D. Seebach, Angew. Chem., Int. Ed. Engl., 1983, 22, 31.
15. For reviews on synthesis of butyrolactones, see: S. Kano, S. Shibuya and T. Ebata, Heterocycles, 1980, 14, 661; Y. S. Rao, Chem. Rev., 1976, 76, 625.
16. For reviews on synthesis of butyrolactones, see: S. Kano, S. Shibuya and T. Ebata, Heterocycles, 1980, 14, 661; Y. S. Rao, Chem. Rev., 1976, 76, 625.