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).
Straightforward Enantioselective Access to γ‑Butyrolactones Bearing an All-Carbon β‑Quaternary Stereocenter
MENINNO, SARA;FUOCO, TIZIANA;TEDESCO, Consiglia;LATTANZI, Alessandra
2014-01-01
Abstract
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).File in questo prodotto:
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