Straightforward Enantioselective Access to γ‑Butyrolactones Bearing an All-Carbon β‑Quaternary Stereocenter

An enantioselective one-pot aldol/lactonization sequence has been developed to access highly challenging γ-butyrolactones bearing an all-carbon quaternary stereocenter at the β-position by reacting acylated succinic esters with aqueous formaldehyde in the presence of 3 mol % loading of a cinchona al...

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Veröffentlicht in:Organic letters 2014-09, Vol.16 (18), p.4746-4749
Hauptverfasser: Meninno, Sara, Fuoco, Tiziana, Tedesco, Consiglia, Lattanzi, Alessandra
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Sprache:eng
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Zusammenfassung:An enantioselective one-pot aldol/lactonization sequence has been developed to access highly challenging γ-butyrolactones bearing an all-carbon quaternary stereocenter at the β-position by reacting acylated succinic esters with aqueous formaldehyde in the presence of 3 mol % loading of a cinchona alkaloid-derived squaramide providing direct access to paraconic acid derivatives in high yield and fairly good level of enantioselectivity (up to 88% ee).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502148a