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 |
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Hauptverfasser: | , , , |
Format: | Artikel |
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). |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol502148a |