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Volumn , Issue 10, 2001, Pages 2001-2009

An efficient synthesis of highly functionalised 4-substituted 2-azetidinones by a stereoselective intermolecular Diels-Alder reaction of different types of 2-azetidinone-tethered dienes

Author keywords

Asymmetric synthesis; Carbocycles; Cycloaddition; Lactams; Retro reactions

Indexed keywords

2 AZETIDINONE DERIVATIVE; ALKADIENE; ANTIINFECTIVE AGENT; BETA LACTAM DERIVATIVE;

EID: 0035016250     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200105)2001:10<2001::aid-ejoc2001>3.3.co;2-d     Document Type: Article
Times cited : (14)

References (59)
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    • (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, Chapter 4.1
    • For a review on the intermolecular Diels-Alder reaction, see: W. Oppolzer, Combining C-C π-bonds, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991; Vol. 5, Chapter 4.1.
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    • note
    • In reference 11 it has been claimed, on the basis of a COSY experiment, that by reaction of racemic trans-3-butadienyl-2-azetidinones with dimethyl acetylenedicarboxylate, a conjugate diene was formed. However, NOE irradiation of vinylic protons on compounds 7a, 7b and 7e resulted, respectively, in 5, 6 and 5% enhancements of the signals corresponding to H1′, which is in agreement with the proposed nonconjugated structure. [16] Considering the diversity of the nomenclature which is used to define facial stereoselectivity in Diels-Alder reactions with chiral dienes with a stereogenic allylic substituent, it is necessary to indicate our choice. In the depicted conformation (see Figure 2), which could not be the reactive one, syn addition refers to the unlike addition, following the Seebach-Prelog convention.
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    • For the preparation of relatively inaccessible 3-monosubstituted and 3,4-disubstituted furans by way of a tandem Diels-Alder/ retro-Diels-Alder reaction, see: [18a] D. Liotta, D. M. Saindane, W. Ott, Tetrahedron Lett. 1983, 24, 2473.
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    • note
    • The structure of cycloadducts 14 was tentatively assigned on the basis of NMR techniques as the exo-endo and the exo-exo isomers, and is in good agreement with previous reports (see reference 20). However, we were unable to obtain totally satisfactory analytical data. (Chemical Equation Presented)
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    • For tandem Diels-Alder processes about reactions of furans with dienophiles, see: [20a] M. Lautens, E. Fillion, J. Org. Chem. 1996, 61, 7994.
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    • note
    • 2. Crystallographic data (excluding structure factors) for the structure included in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-150137. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1223/336-033; Email: deposit@ccdc.cam.ac.uk].
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    • note
    • Full spectroscopic and analytical data for compounds not included in the Experimental Section are provided in the Supporting Information (see footnote on the first page of this article).


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