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Volumn 50, Issue 51, 2009, Pages 7141-7143

Synthesis of pyrrolidin-3-ones from dihydropyran precursors via spiro-N,O-acetals

Author keywords

[No Author keywords available]

Indexed keywords

2 FORMYLDIHYDROPYRAN; ACETAL DERIVATIVE; INDOLIZIDINE ALKALOID; PYRAN DERIVATIVE; PYRROLIDIN 3 ONE; PYRROLIDINE DERIVATIVE; PYRROLIZIDINE ALKALOID; QUINOLIZIDINE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 70350438577     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.10.018     Document Type: Article
Times cited : (11)

References (40)
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    • Åhman J., and Somfai P. Tetrahedron 48 (1992) 9537-9544 For reviews on related N-acyliminium ion chemistry
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    • note
    • int = 0.016), final wR = 0.116. CCDC 745600 contains the full crystallographic data for this compound; this can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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    • The lowest energy conformation for each diastereomer (semi-empirical search) was used to derive a ΔH value at various levels of theory (PM3, HF/6-31G*, B3LYP/6-31G*, MP2/6-31G*, All methods showed isomer 11 to be more stable, ΔH increasing with increasing sophistication in the basis set, with the absolute values being sensitive to small peripheral conformational changes e.g, rotation about the Ar-Me bond, Spartan'06, Wavefunction, Inc, Irvine, CA: Shao, Y, Molnar, L. F, Jung, Y, Kussmann, J, Ochsenfeld, C, Brown, S. T, Gilbert, A. T. B, Slipchenko, L. V, Levchenko, S. V, O'Neill, D. P, DiStasio, R. A, Jr, Lochan, R. C, Wang, T, Beran, G. J. O, Besley, N. A, Herbert, J. M, Lin, C. Y, Van Voorhis, T, Chien, S. H, Sodt, A, Steele, R. P, Rassolov, V. A, Maslen, P. E, Korambath, P. P, Adamson, R. D, Austin, B, Baker, J, Byrd, E. F. C, Dachsel, H, Doerksen, R. J, Dreuw, A, Dunietz, B. D, Dutoi, A. D, Furlani, T. R, Gwaltne
    • The lowest energy conformation for each diastereomer (semi-empirical search) was used to derive a ΔH value at various levels of theory (PM3, HF/6-31G*, B3LYP/6-31G*, MP2/6-31G*). All methods showed isomer 11 to be more stable, ΔH increasing with increasing sophistication in the basis set, with the absolute values being sensitive to small peripheral conformational changes (e.g., rotation about the Ar-Me bond). Spartan'06, Wavefunction, Inc., Irvine, CA: Shao, Y.; Molnar, L. F.; Jung, Y.; Kussmann, J.; Ochsenfeld, C.; Brown, S. T.; Gilbert, A. T. B.; Slipchenko, L. V.; Levchenko, S. V.; O'Neill, D. P.; DiStasio, R. A., Jr.; Lochan, R. C.; Wang, T.; Beran, G. J. O.; Besley, N. A.; Herbert, J. M.; Lin, C. Y.; Van Voorhis, T.; Chien, S. H.; Sodt, A.; Steele, R. P.; Rassolov, V. A.; Maslen, P. E.; Korambath, P. P.; Adamson, R. D.; Austin, B.; Baker, J.; Byrd, E. F. C.; Dachsel, H.; Doerksen, R. J.; Dreuw, A.; Dunietz, B. D.; Dutoi, A. D.; Furlani, T. R.; Gwaltney, S. R.; Heyden, A.; Hirata, S.; Hsu, C.-P.; Kedziora, G.; Khalliulin, R. Z.; Klunzinger, P.; Lee, A. M.; Lee, M. S.; Liang, W. Z.; Lotan, I.; Nair, N.; Peters, B.; Proynov, E. I.; Pieniazek, P. A.; Rhee, Y. M.; Ritchie, J.; Rosta, E.; Sherrill, C. D.; Simmonett, A. C.; Subotnik, J. E.; Woodcock, H. L., III; Zhang, W.; Bell, A. T.; Chakraborty, A. K.; Chipman, D. M.; Keil, F. J.; Warshel, A.; Hehre, W. J.; Schaefer, H. F.; Kong, J.; Krylov, A. I.; Gill, P. M. W.; Head-Gordon, M. Phys. Chem. Chem. Phys. 2006, 8, 3172-3191.
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    • Whilst there are no direct N-sulfonyliminium precedents to draw from, an example of N-acyliminium quenching by [1,2]-H shift from an adjacent hydroxy has been reported in a related system:
    • Whilst there are no direct N-sulfonyliminium precedents to draw from, an example of N-acyliminium quenching by [1,2]-H shift from an adjacent hydroxy has been reported in a related system:. Chien C.S., Hasegawa A., Kawasaki T., and Sakamoto M. Chem. Pharm. Bull. 34 (1986) 1493-1496
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    • Chien, C.S.1    Hasegawa, A.2    Kawasaki, T.3    Sakamoto, M.4
  • 33
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    • The relative nucleophilicity of allylic silanes and stannanes is discussed in:
    • The relative nucleophilicity of allylic silanes and stannanes is discussed in:. Hagen G., and Mayr H. J. Am. Chem. Soc. 113 (1991) 4954-4961
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    • Hagen, G.1    Mayr, H.2
  • 40
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    • note
    • The relative stereochemistry in 22 was not assigned.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.