title: Indium(III)-catalyzed asymmetric hetero-Diels-Alder reaction of Brassard-type diene with aliphatic aldehydes.
abstract: A highly diastereo- and enantioselective hetero-Diels-Alder (HDA) reaction of a Brassard-type diene with aliphatic aldehydes has been developed. The chiral N,N'-dioxide L2/In(OTf)(3) complex was efficient toward the obtention of the corresponding β-methoxy-γ-methyl α,β-unsaturated δ-lactones in good yields (up to 86%) as well as dr and ee values (up to 97:3 cis/trans and 94% ee). In addition, the product 4a could be easily transformed into the methyl-protected epi-prelactone B by hydrogenation.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Yulong
authors.initials: Y
authors.lastname: Kuang
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D007204:Indium / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D008024:Ligands; D007204:Indium