Sequential Rh(I)/Pd-Catalyzed 1,4-Addition/Intramolecular Allylation:  Stereocontrolled Construction of γ-Butyrolactones and Cyclopropanes

Sequential Rh(I)/Pd-Catalyzed 1,4-Addition/Intramolecular Allylation:  Stereocontrolled Construction of γ-Butyrolactones and Cyclopropanes

The rhodium-catalyzed conjugate addition of functionalized vinyltin reagents to alkylidene Meldrum's acids, followed by Pd-catalyzed intramolecular allylation, is a direct entry into vinyl-substituted γ-lactones via O-alkylation and vinylcyclopropanes via C-alkylation.

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Veröffentlicht in:Organic letters 2008-02, Vol.10 (3), p.437-440
Hauptverfasser: Fillion, Eric, Carret, Sébastien, Mercier, Lauren G, Trépanier, Vincent É
Format: Artikel
Sprache:eng
Schlagworte:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
4-Butyrolactone - chemistry
Alkylation
Catalysis
Chemical Sciences
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Palladium - chemistry
Rhodium - chemistry
Stereoisomerism
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Beschreibung
Zusammenfassung:The rhodium-catalyzed conjugate addition of functionalized vinyltin reagents to alkylidene Meldrum's acids, followed by Pd-catalyzed intramolecular allylation, is a direct entry into vinyl-substituted γ-lactones via O-alkylation and vinylcyclopropanes via C-alkylation.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702613f