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Volumn , Issue 28, 2008, Pages 4769-4783

The preparation of α-alkylidene-γ-butyrolactones using a telescoped intramolecular Michael/Olefination (TIMO) sequence: Synthesis of (+)-paeonilactone B

Author keywords

Horner Wadsworth Emmons; Lactones; Michael addition; Phosphonates; Tandem reactions

Indexed keywords


EID: 53849094814     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800558     Document Type: Article
Times cited : (29)

References (75)
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    • For recent intramolecular Michael publications, see: a) M. T. H. Fonseca, B. List, Angew. Chem. Int. Ed. 2004, 43, 3958-3960;
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    • For other conjugate addition/Wittig-Horner sequences, see: a O. Piva, S. Comesse, Eur. J. Org. Chem. 2000, 2417-2424;
    • For other conjugate addition/Wittig-Horner sequences, see: a) O. Piva, S. Comesse, Eur. J. Org. Chem. 2000, 2417-2424;
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    • Details have been deposited at the Cambridge Crystallographic Data Centre (CCDC-658935).
    • Details have been deposited at the Cambridge Crystallographic Data Centre (CCDC-658935).
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    • Details have been deposited at the Cambridge Crystallographic Data Centre (CCDC-659261).
    • Details have been deposited at the Cambridge Crystallographic Data Centre (CCDC-659261).
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    • Details have been deposited at the Cambridge Crystallographic Data Centre (CCDC-658922).
    • Details have been deposited at the Cambridge Crystallographic Data Centre (CCDC-658922).
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    • Details have been deposited at the Cambridge Crystallographic Data Centre (CCDC-686541).
    • Details have been deposited at the Cambridge Crystallographic Data Centre (CCDC-686541).
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    • The related process involving intramolecular epoxide opening with a keto-phosphonate-derived enolate, followed by proton transfer and subsequent HWE olefination was also explored, but without success
    • The related process involving intramolecular epoxide opening with a keto-phosphonate-derived enolate, followed by proton transfer and subsequent HWE olefination was also explored, but without success.
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    • The palladium-catalysed alkylation of allylic carbonates can proceed without addition of an external base as alkoxide is generated from the carbonate anion in situ J. Tsuji, I. Shimizu, I. Minami, Y. Ohashi, T. Sugiura, K. Takahashi, J. Org. Chem. 1985, 50, 1523-1529, Unfortunately, an external base was essential for reaction of carbonate 50
    • The palladium-catalysed alkylation of allylic carbonates can proceed without addition of an external base as alkoxide is generated from the carbonate anion in situ (J. Tsuji, I. Shimizu, I. Minami, Y. Ohashi, T. Sugiura, K. Takahashi, J. Org. Chem. 1985, 50, 1523-1529). Unfortunately, an external base was essential for reaction of carbonate 50.


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