title: Catalytic asymmetric intramolecular homologation of ketones with α-diazoesters: synthesis of cyclic α-aryl/alkyl β-ketoesters.
abstract: A catalytic asymmetric intramolecular homologation of simple ketones with α-diazoesters was firstly accomplished with a chiral N,N'-dioxide-Sc(OTf)3 complex. This method provides an efficient access to chiral cyclic α-aryl/alkyl β-ketoesters containing an all-carbon quaternary stereocenter. Under mild conditions, a variety of aryl- and alkyl-substituted ketone groups reacted with α-diazoester groups smoothly through an intramolecular addition/rearrangement process, producing the β-ketoesters in high yield and enantiomeric excess.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China).
authors.forename: Wei
authors.initials: W
authors.lastname: Li
authors.forename: Fei
authors.initials: F
authors.lastname: Tan
authors.forename: Xiaoyu
authors.initials: X
authors.lastname: Hao
authors.forename: Gang
authors.initials: G
authors.lastname: Wang
authors.forename: Yu
authors.initials: Y
authors.lastname: Tang
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
keywords: asymmetric catalysis; homologation; scandium; α-diazoesters; β-ketoesters