title: Catalytic enantioselective synthesis of chiral γ-butyrolactones.
abstract: A tandem catalytic asymmetric aldol reaction/cyclization of β,γ-didehydro-γ-lactones with aldehydes was achieved using chiral tin dibromide as a chiral precatalyst and sodium alkoxide as a base precatalyst. Optically active trans-β,γ-disubstituted γ-butyrolactones were selectively obtained in moderate to high yields with up to 99% ee from γ-aryl-substituted β,γ-didehydro-γ-butyrolactones and bulky aliphatic aldehydes.
authors.affiliation: Department of Chemistry, Graduate School of Science, Chiba University, Chiba 263-8522, Japan. ayanagi@faculty.chiba-u.jp
authors.forename: Akira
authors.initials: A
authors.lastname: Yanagisawa
authors.forename: Naoyuki
authors.initials: N
authors.lastname: Kushihara
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Yoshida
mesh_terms: D015107:4-Butyrolactone / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D015107:4-Butyrolactone