title: Magnesium(II)-catalyzed asymmetric hetero-Diels-Alder reaction of Brassard's dienes with isatins.
abstract: The first catalytic asymmetric hetero-Diels-Alder reaction of Brassard's dienes with isatins was realized using Mg(II)/N,N'-dioxide complexes as catalysts, affording the corresponding chiral spirolactones bearing tetrasubstituted centers in up to 99% yield with up to 99% ee and >99 : 1 dr within 3 hours. In the mechanism, based on the operando IR experiments, a predominant Diels-Alder pathway was found in the reaction. A possible transition state model was also proposed.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China. xmfeng@scu.edu.cn.
authors.forename: Jianfeng
authors.initials: J
authors.lastname: Zheng
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Yulong
authors.initials: Y
authors.lastname: Kuang
authors.forename: Jiannan
authors.initials: J
authors.lastname: Zhao
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D061565:Cycloaddition Reaction; D007477:Ions / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; C510429:Brassard's diene; D056831:Coordination Complexes; D007477:Ions; D014297:Trimethylsilyl Compounds; D007510:Isatin; D008274:Magnesium