title: Asymmetric Michael addition of N-tert-butanesulfinyl imidate with α,β-unsaturated diesters: scope and application to the synthesis of indanone derivatives.
abstract: An additive-free and highly diastereoselective Michael addition reaction of an N-tert-butanesulfinyl imidate to α,β-unsaturated diesters has been developed using LDA as a base with good to excellent yields. The utility of this chemistry is further demonstrated by the asymmetric synthesis of 3-substituted indanone derivatives 8a, 8d, 8e, and 8i with high enantiomeric excess, which are potential building blocks for preparing biologically active lead compounds.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China.
authors.forename: Jinfang
authors.initials: J
authors.lastname: Wang
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhou
authors.forename: Lei
authors.initials: L
authors.lastname: Zhang
authors.forename: Zeng
authors.initials: Z
authors.lastname: Li
authors.forename: Xianjie
authors.initials: X
authors.lastname: Chen
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
mesh_terms: D002384:Catalysis; D007096:Imidoesters / Q000737:chemistry*; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D007096:Imidoesters; D007189:Indans; D013452:Sulfonium Compounds