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Volumn 40, Issue 29, 1999, Pages 5391-5394

Rapid entry to enantiopure polycyclic β-lactams via intramolecular nitrone-alkene cycloaddition of 2-azetidinone-tethered alkenylaldehydes

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; ALDEHYDE; BETA LACTAM;

EID: 0033575466     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01013-8     Document Type: Article
Times cited : (25)

References (41)
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    • INAC reactions of aliphatic 2-substituted 5-hexenyl and 5-heptenyl nitrones have been successfully used for the synthesis of key monocyclic intermediates of 1β-methylthienamycin. A notable feature of such processes is their propensity for the predominant formation of the fused bicyclic systems as opposed to the bridged systems. See, for example: a) Kang, S. H.; Kim, W. J. Synlett. 1991, 520. b) Kang, S. H.; Lee, H. S. Tetrahedron Lett. 1995, 36, 6713. b) Junk, M. E.;Vu, B. T. J. Org. Chem. 1996, 61, 4427.
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    • INAC reactions of aliphatic 2-substituted 5-hexenyl and 5-heptenyl nitrones have been successfully used for the synthesis of key monocyclic intermediates of 1β-methylthienamycin. A notable feature of such processes is their propensity for the predominant formation of the fused bicyclic systems as opposed to the bridged systems. See, for example: a) Kang, S. H.; Kim, W. J. Synlett. 1991, 520. b) Kang, S. H.; Lee, H. S. Tetrahedron Lett. 1995, 36, 6713. b) Junk, M. E.;Vu, B. T. J. Org. Chem. 1996, 61, 4427.
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    • For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a) Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
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    • For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
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    • For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a) Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
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    • For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a) Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
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    • See, for instance: a) van Boggelen, M. P.; van Dommelen, B. F. G. A.; Jiang, Sh.; Singh, G. Tetrahedron 1997, 53, 16897. b) Tsay, S.-C.; Patel, H. V.; Hwu, J. R. Synlett. 1998, 939.
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    • -1; F(000) = 552. A colourless crystal of 0.66×0.16×0.16 mm was used. 1210 independent reflections were collected on four circle Seifert XRD 3000S difractometer. The structure was solved by direct methods (SIR92 and difference Fourier techniques; not absorption correction was applied (m = 0.79 mm-1); all calculations were done with the program SHELX97 on a VAX 6410 computer. The structure was refined using full matrix least-squares procedures. Coordinates have been deposited at the Cambridge Crystallographic Data Centre. Figure. Crystal structure of (-)-3a (equation presented)
    • -1; F(000) = 552. A colourless crystal of 0.66×0.16×0.16 mm was used. 1210 independent reflections were collected on four circle Seifert XRD 3000S difractometer. The structure was solved by direct methods (SIR92 and difference Fourier techniques; not absorption correction was applied (m = 0.79 mm-1); all calculations were done with the program SHELX97 on a VAX 6410 computer. The structure was refined using full matrix least-squares procedures. Coordinates have been deposited at the Cambridge Crystallographic Data Centre. Figure. Crystal structure of (-)-3a (equation presented)
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    • See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
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    • 0013622773 scopus 로고    scopus 로고
    • The salient features which distinguished between the two regioisomers (2a and 3a, for example) was the presence, in the NMR spectrum of compound 2a, of a highfield one proton multiplet at δ(H) 2.78 coupled to five other protons and a methine carbon signal at δ(C) 37.8 (DEPT), which would be expected for the C-8 methine in the fused structure 2a. Also, this compound showed two methylene carbon resonances at δ(C) 60.8 and 68.6 (DEPT) attributable to two oxygen substituted methylene carbons. Compound 3a displayed a highfield geminally coupled (12.7 Hz) proton signals at δ(H) 2.40 (m) and 1.92 (d), and a methylene carbon resonance at δ(C)28.5 (DEPT), and was consistent with its bridged structure
    • The salient features which distinguished between the two regioisomers (2a and 3a, for example) was the presence, in the NMR spectrum of compound 2a, of a highfield one proton multiplet at δ(H) 2.78 coupled to five other protons and a methine carbon signal at δ(C) 37.8 (DEPT), which would be expected for the C-8 methine in the fused structure 2a. Also, this compound showed two methylene carbon resonances at δ(C) 60.8 and 68.6 (DEPT) attributable to two oxygen substituted methylene carbons. Compound 3a displayed a highfield geminally coupled (12.7 Hz) proton signals at δ(H) 2.40 (m) and 1.92 (d), and a methylene carbon resonance at δ(C)28.5 (DEPT), and was consistent with its bridged structure.
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    • 0013571228 scopus 로고    scopus 로고
    • All new compounds gave satisfactory analytical and spectral data
    • All new compounds gave satisfactory analytical and spectral data.


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