title: Straightforward enantioselective access to γ-butyrolactones bearing an all-carbon β-quaternary stereocenter.
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).
authors.affiliation: Dipartimento di Chimica e Biologia, Università di Salerno , Via Giovanni Paolo II, 84084 Fisciano, Italy.
authors.forename: Sara
authors.initials: S
authors.lastname: Meninno
authors.forename: Tiziana
authors.initials: T
authors.lastname: Fuoco
authors.forename: Consiglia
authors.initials: C
authors.lastname: Tedesco
authors.forename: Alessandra
authors.initials: A
authors.lastname: Lattanzi
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013386:Succinates / Q000737:chemistry
chemical_list: D002930:Cinchona Alkaloids; D013386:Succinates; C571316:paraconic acid; D015107:4-Butyrolactone