title: Zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous media: an efficient synthesis method for α-methylene-γ-butyrolactone.
abstract: A zinc or indium-mediated Barbier-type allylation of aldehydes with 3-bromomethyl-5H-furan-2-one in aqueous solvents was developed to provide an efficient route to α-methylene-γ-butyrolactone, which is synthetically very useful. The desired products were obtained in moderate to high yields in aqueous solvents. Excellent drs were achieved, among which the best diastereomeric ratios of products were found when water was used in the indium-mediated reaction, and THF-NH(4)Cl (sat, aq) (2 : 1) mixture in the zinc-mediated reaction. Furthermore, the allylation can be induced by chiral centers, especially those in the α-position, as a substrate-controlled reaction to obtain the enantioselective homoallylation alcohols.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.
authors.forename: YuZhe
authors.initials: Y
authors.lastname: Gao
authors.forename: Xue
authors.initials: X
authors.lastname: Wang
authors.forename: LiDong
authors.initials: L
authors.lastname: Sun
authors.forename: LongGuan
authors.initials: L
authors.lastname: Xie
authors.forename: XiaoHua
authors.initials: X
authors.lastname: Xu
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000447:Aldehydes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry; D015032:Zinc / Q000737:chemistry*
chemical_list: C574254:3-bromomethyl-5H-furan-2-one; D000447:Aldehydes; D005663:Furans; D012997:Solvents; D007204:Indium; C014096:alpha-methylene gamma-butyrolactone; D015032:Zinc; D015107:4-Butyrolactone