title: A new entry to asymmetric synthesis of optically active alpha,gamma-substituted gamma-butyrolactones, using a carbohydrate derived amide as both a chiral auxiliary and a proton source.
abstract: A new entry for the asymmetric synthesis of optically active alpha,gamma-substituted gamma-butyrolactones was developed by using a carbohydrate-derived amide as both a chiral auxiliary and a proton source. Unlike the previously reported examples, the chiral auxiliary employed in this reaction also successfully functioned as a protonating agent. Excellent asymmetric induction could be achieved by this dual stereoselective control in the reaction process.
authors.affiliation: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
authors.forename: Ling-Lin
authors.initials: LL
authors.lastname: Huang
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Xu
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Lin
mesh_terms: D015107:4-Butyrolactone / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D015394:Molecular Structure; D009904:Optical Rotation; D011522:Protons; D013237:Stereoisomerism
chemical_list: D000577:Amides; D011522:Protons; D015107:4-Butyrolactone