title: Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives.
abstract: A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.
authors.affiliation: Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C.
authors.forename: Shu-Mei
authors.initials: SM
authors.lastname: Yang
authors.affiliation: Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C.
authors.forename: Ganapuram
authors.initials: G
authors.lastname: Madhusudhan Reddy
authors.affiliation: Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C.
authors.forename: Meng-Hsien
authors.initials: MH
authors.lastname: Liu
authors.affiliation: Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C.
authors.forename: Tzu-Ping
authors.initials: TP
authors.lastname: Wang
authors.affiliation: Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C.
authors.forename: Jhen-Kuei
authors.initials: JK
authors.lastname: Yu
authors.affiliation: Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C.
authors.forename: Wenwei
authors.identifier: 0000-0002-1121-072X
authors.initials: W
authors.lastname: Lin