Reactions of β,γ- and γ,δ-unsaturated esters with the reagent Ti(O/Pr)4/2iPrMgCl: formation of β-titanated esters, β-titanated cyclobutanones, and acyltitanium compounds

Angewandte Chemie (International Edition in English)

Volumn 35, Issue 17, 1996, Pages 1966-1968

  Kasatkin, Aleksandr ^a   Yamazaki, Takanori ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Alkenes; Alkynes; Cyclizations; Cyclobutanones; Titanium compounds

Indexed keywords

EID: 0029985016     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199619661     Document Type: Article

References (13)

1. A. Kasatkin, T. Nakagawa, S. Okamoto, F. Sato, J. Am. Chem. Soc. 1995, 117, 3881; O.G. Kulinkovich, S.V. Sviridov, D.A. Vasilevskii, Synthesis 1991, 234.
2. A. Kasatkin, T. Nakagawa, S. Okamoto, F. Sato, J. Am. Chem. Soc. 1995, 117, 3881; O.G. Kulinkovich, S.V. Sviridov, D.A. Vasilevskii, Synthesis 1991, 234.
3. T. Yamazaki, A. Kasatkin, Y. Kawanaka, F. Sato, J. Org. Chem. 1996, 61, 2266.
4. T. Nakagawa, A. Kasatkin, F. Sato, Tetrahedron Lett. 1995, 36, 3207.
5. K. Harada, H. Urabe, F. Sato, Tetrahedron Lett. 1995, 36, 3203.
6. For preparation of the compounds of type 3 and their application in organic synthesis, see: H. Stetter, K. Marten, Liebigs Ann. Chem. 1982, 240; H. Amri, M. Rambaud, J. Villieras, Tetrahedron Lett. 1989, 30, 7381; A. M. Moiseenkov, B. Ceskis, N. A. Shapiro, G. A. Stashina, V. M. Zhulin, I. Akad. Nauk SSSR Ser. Khim. 1990, 595; S. E. Drewes, N. D. Emslie, N. Karodia, G. Loizou, Synth. Commun. 1990, 20, 1437; J. Tanaka, S. Kanemasa, Y Ninomiya, O. Tsuge, Bull. Chem. Soc. Jpn 1990, 63, 466.
7. For preparation of the compounds of type 3 and their application in organic synthesis, see: H. Stetter, K. Marten, Liebigs Ann. Chem. 1982, 240; H. Amri, M. Rambaud, J. Villieras, Tetrahedron Lett. 1989, 30, 7381; A. M. Moiseenkov, B. Ceskis, N. A. Shapiro, G. A. Stashina, V. M. Zhulin, I. Akad. Nauk SSSR Ser. Khim. 1990, 595; S. E. Drewes, N. D. Emslie, N. Karodia, G. Loizou, Synth. Commun. 1990, 20, 1437; J. Tanaka, S. Kanemasa, Y Ninomiya, O. Tsuge, Bull. Chem. Soc. Jpn 1990, 63, 466.
8. For preparation of the compounds of type 3 and their application in organic synthesis, see: H. Stetter, K. Marten, Liebigs Ann. Chem. 1982, 240; H. Amri, M. Rambaud, J. Villieras, Tetrahedron Lett. 1989, 30, 7381; A. M. Moiseenkov, B. Ceskis, N. A. Shapiro, G. A. Stashina, V. M. Zhulin, I. Akad. Nauk SSSR Ser. Khim. 1990, 595; S. E. Drewes, N. D. Emslie, N. Karodia, G. Loizou, Synth. Commun. 1990, 20, 1437; J. Tanaka, S. Kanemasa, Y Ninomiya, O. Tsuge, Bull. Chem. Soc. Jpn 1990, 63, 466.
9. For preparation of the compounds of type 3 and their application in organic synthesis, see: H. Stetter, K. Marten, Liebigs Ann. Chem. 1982, 240; H. Amri, M. Rambaud, J. Villieras, Tetrahedron Lett. 1989, 30, 7381; A. M. Moiseenkov, B. Ceskis, N. A. Shapiro, G. A. Stashina, V. M. Zhulin, I. Akad. Nauk SSSR Ser. Khim. 1990, 595; S. E. Drewes, N. D. Emslie, N. Karodia, G. Loizou, Synth. Commun. 1990, 20, 1437; J. Tanaka, S. Kanemasa, Y Ninomiya, O. Tsuge, Bull. Chem. Soc. Jpn 1990, 63, 466.
10. For preparation of the compounds of type 3 and their application in organic synthesis, see: H. Stetter, K. Marten, Liebigs Ann. Chem. 1982, 240; H. Amri, M. Rambaud, J. Villieras, Tetrahedron Lett. 1989, 30, 7381; A. M. Moiseenkov, B. Ceskis, N. A. Shapiro, G. A. Stashina, V. M. Zhulin, I. Akad. Nauk SSSR Ser. Khim. 1990, 595; S. E. Drewes, N. D. Emslie, N. Karodia, G. Loizou, Synth. Commun. 1990, 20, 1437; J. Tanaka, S. Kanemasa, Y Ninomiya, O. Tsuge, Bull. Chem. Soc. Jpn 1990, 63, 466.
11. We found that 7 reacts with PhCHO selectively at the titanium enolate moiety to furnish after hydrolysis the corresponding x-alkylidene-x′-(hydroxybenzyl)-glutarates.
12. A. Kasatkin, S. Okamoto, F. Sato, Tetrahedron Lett. 1995, 36, 6075; S. Okamoto, A. Kasatkin, P. K. Zubaidha, F. Sato, J. Am. Chem. Soc. 1996, 118, 2208.
13. A. Kasatkin, S. Okamoto, F. Sato, Tetrahedron Lett. 1995, 36, 6075; S. Okamoto, A. Kasatkin, P. K. Zubaidha, F. Sato, J. Am. Chem. Soc. 1996, 118, 2208.