Diastereoselective Construction of Trans-Fused Octalone Framework via Ruthenium-Porphyrin-Catalyzed Cycloaddition

Lewis acid catalyzed cycloaddition of cyclohexenone and butadiene affords trans-fused octalone with high regio- and diastereoselectivity. The use of the ruthenium porphyrin complex as the Lewis acid catalyst is key to the reaction. The cycloaddition proceeds in toluene with 1 mol % of the ruthenium...

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Veröffentlicht in:	Organic letters 2014-05, Vol.16 (10), p.2594-2597
Hauptverfasser:	Terada, Takuma, Kurahashi, Takuya, Matsubara, Seijiro
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Cycloaddition Reaction Cyclohexanones - chemistry Lewis Acids - chemistry Models, Molecular Molecular Structure Porphyrins - chemistry Ruthenium - chemistry Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	Lewis acid catalyzed cycloaddition of cyclohexenone and butadiene affords trans-fused octalone with high regio- and diastereoselectivity. The use of the ruthenium porphyrin complex as the Lewis acid catalyst is key to the reaction. The cycloaddition proceeds in toluene with 1 mol % of the ruthenium catalyst at 25 °C.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol500625r