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Volumn 59, Issue 2, 2003, Pages 241-248

Cyclization and rearrangement of 4-(2-methyloxiranyl)-β-lactams promoted by titanocene dichloride/Zn0

Author keywords

Carbapenam; Epoxy lactams; Ring expansion; Titanocene; Tribactam

Indexed keywords

AZETIDINONE DERIVATIVE; BETA LACTAM DERIVATIVE; GLUCOSAMINE; TITANOCENE DICHLORIDE; ZINC DERIVATIVE;

EID: 0037421138     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01459-X     Document Type: Article
Times cited : (31)

References (34)
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    • For a review on cyclization methodologies to prepare bicyclic (β-lactams, see: (a) Kant, J.; Walker, D. G.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams. Georg, G. I., Ed. Strategies for the Synthesis of Bicyclic β-Lactams; VCH: New York, 1993; pp 121-196. Recent examples to the synthesis of trinem derivatives: (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587-3590. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463-468. (d) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884-9891.
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    • For a review on cyclization methodologies to prepare bicyclic (β-lactams, see: (a) Kant, J.; Walker, D. G.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams. Georg, G. I., Ed. Strategies for the Synthesis of Bicyclic β-Lactams; VCH: New York, 1993; pp 121-196. Recent examples to the synthesis of trinem derivatives: (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587-3590. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463-468. (d) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884-9891.
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    • The preferred conformations for epoxides 4 were derived from the CS Chem3D Pro software (CambridgeSoft Corporation) using MM2 calculations
    • The preferred conformations for epoxides 4 were derived from the CS Chem3D Pro software (CambridgeSoft Corporation) using MM2 calculations.
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    • For a similar rearrangement from 4-formyl-2-azetidinones reacting with concentrated sulfuric acid see:
    • For a similar rearrangement from 4-formyl-2-azetidinones reacting with concentrated sulfuric acid see: Alcaide B., Martín-Cantalejo Y., Rodríguez-López J., Sierra M.-A. J. Org. Chem. 58:1993;4767-4770.
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    • Alcaide, B.1    Martín-Cantalejo, Y.2    Rodríguez-López, J.3    Sierra, M.-A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.