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Heterocycles
Volumn 42, Issue 2, 1996, Pages 565-574
Carbometalation of cyclopropenes. Stereoselective synthesis of divinyl ketones via 1,5-hydrogen migration reaction of vinylcyclopropanes
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EID: 0038614393     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s22     Document Type: Article
Times cited : (8)
References (39)
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    • J. P. Daub and J. A. Berson, Tetrahedron Lett., 1984, 25, 4463. The ab initio calculations at HF/3-21G level would still give us only a qualitative estimate of energetics in this 1,5-hydrogen shift reaction: R. J. Loncharich and K. N. Houk, J. Am. Chem. Soc., 1988, 110, 2089.
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    • J. P. Daub and J. A. Berson, Tetrahedron Lett., 1984, 25, 4463. The ab initio calculations at HF/3-21G level would still give us only a qualitative estimate of energetics in this 1,5-hydrogen shift reaction: R. J. Loncharich and K. N. Houk, J. Am. Chem. Soc., 1988, 110, 2089.
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    • (b) E. Nakamura, M. Isaka, and S. Matsuzawa, J. Am. Chem. Soc., 1988, 110, 1297. Cf. K. Kubota, M. Isaka, M. Nakamura, and E. Nakamura, J. Am. Chem. Soc., 1993, 115, 5867; M. Nakamura, M. Arai, and E. Nakamura, J. Am. Chem. Soc., 1995, 117, 1179; E. Nakamura, J. Syn. Org. Chem., Jpn., 1993, 51, 985. Theoretical study of carbometalation of cyclopropane: E. Nakamura, M. Nakamura, Y. Miyachi, N. Koga, and K. Morokuma, J. Am. Chem. Soc., 1993, 115, 1789: Nakamura, E. Nakamura, N. Koga, and K. Morokuma, J. Chem. Soc. Faraday Trans., 1994, 90, 1789.
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    • (b) E. Nakamura, M. Isaka, and S. Matsuzawa, J. Am. Chem. Soc., 1988, 110, 1297. Cf. K. Kubota, M. Isaka, M. Nakamura, and E. Nakamura, J. Am. Chem. Soc., 1993, 115, 5867; M. Nakamura, M. Arai, and E. Nakamura, J. Am. Chem. Soc., 1995, 117, 1179; E. Nakamura, J. Syn. Org. Chem., Jpn., 1993, 51, 985. Theoretical study of carbometalation of cyclopropane: E. Nakamura, M. Nakamura, Y. Miyachi, N. Koga, and K. Morokuma, J. Am. Chem. Soc., 1993, 115, 1789: Nakamura, E. Nakamura, N. Koga, and K. Morokuma, J. Chem. Soc. Faraday Trans., 1994, 90, 1789.
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    • (b) E. Nakamura, M. Isaka, and S. Matsuzawa, J. Am. Chem. Soc., 1988, 110, 1297. Cf. K. Kubota, M. Isaka, M. Nakamura, and E. Nakamura, J. Am. Chem. Soc., 1993, 115, 5867; M. Nakamura, M. Arai, and E. Nakamura, J. Am. Chem. Soc., 1995, 117, 1179; E. Nakamura, J. Syn. Org. Chem., Jpn., 1993, 51, 985. Theoretical study of carbometalation of cyclopropane: E. Nakamura, M. Nakamura, Y. Miyachi, N. Koga, and K. Morokuma, J. Am. Chem. Soc., 1993, 115, 1789: Nakamura, E. Nakamura, N. Koga, and K. Morokuma, J. Chem. Soc. Faraday Trans., 1994, 90, 1789.
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    • Nakamura, E.1    Nakamura, M.2    Miyachi, Y.3    Koga, N.4    Morokuma, K.5
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    • (b) E. Nakamura, M. Isaka, and S. Matsuzawa, J. Am. Chem. Soc., 1988, 110, 1297. Cf. K. Kubota, M. Isaka, M. Nakamura, and E. Nakamura, J. Am. Chem. Soc., 1993, 115, 5867; M. Nakamura, M. Arai, and E. Nakamura, J. Am. Chem. Soc., 1995, 117, 1179; E. Nakamura, J. Syn. Org. Chem., Jpn., 1993, 51, 985. Theoretical study of carbometalation of cyclopropane: E. Nakamura, M. Nakamura, Y. Miyachi, N. Koga, and K. Morokuma, J. Am. Chem. Soc., 1993, 115, 1789: Nakamura, E. Nakamura, N. Koga, and K. Morokuma, J. Chem. Soc. Faraday Trans., 1994, 90, 1789.
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    • However, the present sequence may also be applicable to simple cyclopropenes, which serve as an acceptor in carbometalation reaction. Cf. E. Nakamura and M. Isaka, Organometallic News, 1990, 194; A. M. Moiseenkov, B, A. Czeskis, and A. V. Semenovsky, J. Chem. Soc., Chem. Commun., 1982, 109; M. Y. Lukina, T. Y. Rudashevskaya, and O. A. Nesmeyanova, Dokl. Akad. Nauk SSSR., 1970, 190, 1109; H. Lehmkuhl and K. Mehler, Liebigs Ann. Chem., 1982, 2244; A. T. Stoll and E.-i. Negishi, Tetrahedron Lett., 1985, 26, 5671. We have found that spiro[2,5]oct-1-ene, an all carbon congener of 2, also serves as a good acceptor of dialkylcuprates: unpublished results.
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    • Nakamura, E.1    Isaka, M.2
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    • However, the present sequence may also be applicable to simple cyclopropenes, which serve as an acceptor in carbometalation reaction. Cf. E. Nakamura and M. Isaka, Organometallic News, 1990, 194; A. M. Moiseenkov, B, A. Czeskis, and A. V. Semenovsky, J. Chem. Soc., Chem. Commun., 1982, 109; M. Y. Lukina, T. Y. Rudashevskaya, and O. A. Nesmeyanova, Dokl. Akad. Nauk SSSR., 1970, 190, 1109; H. Lehmkuhl and K. Mehler, Liebigs Ann. Chem., 1982, 2244; A. T. Stoll and E.-i. Negishi, Tetrahedron Lett., 1985, 26, 5671. We have found that spiro[2,5]oct-1-ene, an all carbon congener of 2, also serves as a good acceptor of dialkylcuprates: unpublished results.
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  • 28
    • 2742589059 scopus 로고
    • However, the present sequence may also be applicable to simple cyclopropenes, which serve as an acceptor in carbometalation reaction. Cf. E. Nakamura and M. Isaka, Organometallic News, 1990, 194; A. M. Moiseenkov, B, A. Czeskis, and A. V. Semenovsky, J. Chem. Soc., Chem. Commun., 1982, 109; M. Y. Lukina, T. Y. Rudashevskaya, and O. A. Nesmeyanova, Dokl. Akad. Nauk SSSR., 1970, 190, 1109; H. Lehmkuhl and K. Mehler, Liebigs Ann. Chem., 1982, 2244; A. T. Stoll and E.-i. Negishi, Tetrahedron Lett., 1985, 26, 5671. We have found that spiro[2,5]oct-1-ene, an all carbon congener of 2, also serves as a good acceptor of dialkylcuprates: unpublished results.
    • (1970) Dokl. Akad. Nauk SSSR. , vol.190 , pp. 1109
    • Lukina, M.Y.1    Rudashevskaya, T.Y.2    Nesmeyanova, O.A.3
  • 29
    • 0002172919 scopus 로고
    • However, the present sequence may also be applicable to simple cyclopropenes, which serve as an acceptor in carbometalation reaction. Cf. E. Nakamura and M. Isaka, Organometallic News, 1990, 194; A. M. Moiseenkov, B, A. Czeskis, and A. V. Semenovsky, J. Chem. Soc., Chem. Commun., 1982, 109; M. Y. Lukina, T. Y. Rudashevskaya, and O. A. Nesmeyanova, Dokl. Akad. Nauk SSSR., 1970, 190, 1109; H. Lehmkuhl and K. Mehler, Liebigs Ann. Chem., 1982, 2244; A. T. Stoll and E.-i. Negishi, Tetrahedron Lett., 1985, 26, 5671. We have found that spiro[2,5]oct-1-ene, an all carbon congener of 2, also serves as a good acceptor of dialkylcuprates: unpublished results.
    • (1982) Liebigs Ann. Chem. , pp. 2244
    • Lehmkuhl, H.1    Mehler, K.2
  • 30
    • 0000718165 scopus 로고
    • We have found that spiro[2,5]oct-1-ene, an all carbon congener of 2, also serves as a good acceptor of dialkylcuprates: unpublished results
    • However, the present sequence may also be applicable to simple cyclopropenes, which serve as an acceptor in carbometalation reaction. Cf. E. Nakamura and M. Isaka, Organometallic News, 1990, 194; A. M. Moiseenkov, B, A. Czeskis, and A. V. Semenovsky, J. Chem. Soc., Chem. Commun., 1982, 109; M. Y. Lukina, T. Y. Rudashevskaya, and O. A. Nesmeyanova, Dokl. Akad. Nauk SSSR., 1970, 190, 1109; H. Lehmkuhl and K. Mehler, Liebigs Ann. Chem., 1982, 2244; A. T. Stoll and E.-i. Negishi, Tetrahedron Lett., 1985, 26, 5671. We have found that spiro[2,5]oct-1-ene, an all carbon congener of 2, also serves as a good acceptor of dialkylcuprates: unpublished results.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5671
    • Stoll, A.T.1    Negishi, E.-I.2
  • 33
    • 2742581436 scopus 로고    scopus 로고
    • The MMX force field implemented in PCModel software: Serena Software, Bloomington, Indiana
    • The MMX force field implemented in PCModel software: Serena Software, Bloomington, Indiana.
  • 35
    • 2742577041 scopus 로고    scopus 로고
    • note
    • Upon removal of this constraint (2.2 Å, with 5 m dyne/Å) the structure relaxes to a local minimum ca. 4 kcal/mol lower in energy. Thus, this structure represents a very early stage toward the transition state.
  • 36
    • 2742573854 scopus 로고    scopus 로고
    • Starting with a pure Z, E-isomer
    • Starting with a pure Z, E-isomer.
  • 37
    • 0001215023 scopus 로고
    • Cf. E. Nakamura, S. Yamago, S. Ejiri, A. E. Dorigo, and K. Morokuma, J. Am. Chem. Soc., 1991, 113, 3183; H. Tokuyama, M. Isaka, and E. Nakamura, J. Am. Chem. Soc., 1992, 114, 5523; T. Fujimura, S. Aoki, and E. Nakamura, J. Org. Chem., 1991, 56, 2809.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 3183
    • Nakamura, E.1    Yamago, S.2    Ejiri, S.3    Dorigo, A.E.4    Morokuma, K.5
  • 38
    • 0001666553 scopus 로고
    • Cf. E. Nakamura, S. Yamago, S. Ejiri, A. E. Dorigo, and K. Morokuma, J. Am. Chem. Soc., 1991, 113, 3183; H. Tokuyama, M. Isaka, and E. Nakamura, J. Am. Chem. Soc., 1992, 114, 5523; T. Fujimura, S. Aoki, and E. Nakamura, J. Org. Chem., 1991, 56, 2809.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5523
    • Tokuyama, H.1    Isaka, M.2    Nakamura, E.3
  • 39
    • 0001703895 scopus 로고
    • Cf. E. Nakamura, S. Yamago, S. Ejiri, A. E. Dorigo, and K. Morokuma, J. Am. Chem. Soc., 1991, 113, 3183; H. Tokuyama, M. Isaka, and E. Nakamura, J. Am. Chem. Soc., 1992, 114, 5523; T. Fujimura, S. Aoki, and E. Nakamura, J. Org. Chem., 1991, 56, 2809.
    • (1991) J. Org. Chem. , vol.56 , pp. 2809
    • Fujimura, T.1    Aoki, S.2    Nakamura, E.3

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.