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Volumn 52, Issue 3, 1996, Pages 1069-1084

A convenient approach to diastereomerically pure 1,3,4-trisubstituted pyrrolidin-2-ones by intramolecular cyclisation of N-(2-alken-1-yl)amides mediated by Mn(III). An entry to both (R)- and (S)-3-pyrrolidineacetic acid

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE;

EID: 0030059325     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00939-6     Document Type: Article
Times cited : (59)

References (47)
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    • For leading references about this approach, see: a) Melikyan, G. Synthesis, 1993, 833-850.
    • (1993) Synthesis , pp. 833-850
    • Melikyan, G.1
  • 17
    • 85029992340 scopus 로고    scopus 로고
    • note
    • 10.
  • 19
    • 0000420637 scopus 로고
    • Analogous results were observed by radical cyclisation of enamides bearing (S)-1-phenylethyl group on the nitrogen atom, leading to β-lactams: a) Ishibashi, H.; Kameoka, C.; Tatsunori, S.; Ikeda, M. Synlett, 1994, 445-446.
    • (1994) Synlett , pp. 445-446
    • Ishibashi, H.1    Kameoka, C.2    Tatsunori, S.3    Ikeda, M.4
  • 22
    • 3042988525 scopus 로고
    • The MM+ force field is an extension of MM2 which was developed by Allinger and co-workers. As references see: a) Allinger, N.L. J. Am. Chem. Soc., 1977, 99, 8127-8134.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 8127-8134
    • Allinger, N.L.1
  • 23
    • 0003323222 scopus 로고
    • Molecular mechanics
    • Quantum Chemistry Program Exchange, Bloomington, Indiana, Program #395, Burkert, U.; Allinger, N.L. edd., American Chemical Society, Washington, D.C.
    • b) Allinger, N.L., Yuh, Y.H., Quantum Chemistry Program Exchange, Bloomington, Indiana, Program #395, Molecular Mechanics, Burkert, U.; Allinger, N.L. edd., ACS Monograph 177, American Chemical Society, Washington, D.C., 1982.
    • (1982) ACS Monograph , vol.177
    • Allinger, N.L.1    Yuh, Y.H.2
  • 25
    • 0006189515 scopus 로고
    • Feb.
    • Lipkowitz, K.B. QCPE Bulletin, Indiana University, 12, 1 (Feb. 1992). The program is enclosed in Hyperchem package, release 4.0, available from Hypercube, Waterloo, Canada.
    • (1992) QCPE Bulletin, Indiana University , vol.12 , pp. 1
    • Lipkowitz, K.B.1
  • 31
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    • e) Orena, M., Porzi, G.; Sandri, S. J. Chem. Res., (S), 1990, 376; (M), 1990, 2701-2711.
    • (1990) J. Chem. Res., (M) , pp. 2701-2711
  • 36
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    • Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res., (S), 1993, 318-319; (M), 1993, 2125-2152.
    • (1993) J. Chem. Res., (M) , pp. 2125-2152
  • 37
    • 85029991557 scopus 로고    scopus 로고
    • note
    • i = 1, k = 1.986 (cal/mol · K), and T = 298 (K).
  • 42
    • 85029991804 scopus 로고    scopus 로고
    • note
    • A similar trend resulted for the heats of formation of the transition states TS', calculated by AM1-UHF method. In fact the following values were found: TS'-1(A): -8.06 kcal/mol, TS'-1(B): -9.19 kcal/mol; TS'-2(A): -8.83 kcal/mol; TS'-2(B): -8.85 kcal/mol.


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