title: An organocatalytic domino Michael-alkylation reaction: highly enantioselective construction of spiro-cyclopentanoneoxindoles and tetronic acid scaffolds.
abstract: A new organocatalytic asymmetric domino Michael-alkylation reaction of methyleneindolinones and γ-halogenated-β-ketoesters is described. A variety of spiro-cyclopentanoneoxindoles were obtained in high yields (up to 96%), good diastereoselectivities (up to 12 : 1 dr) and excellent enantioselectivities (up to >99% ee) via α-alkylation. Interestingly, O-alkylated products with tetronic acid motifs could be obtained by tuning the N-protecting groups on methyleneindolinones with excellent enantioselectivities (up to >99% ee).
authors.affiliation: Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. wlxioc@cioc.ac.cn xuxy@cioc.ac.cn.
authors.forename: Jing
authors.initials: J
authors.lastname: Zhou
authors.forename: Qi-Lin
authors.initials: QL
authors.lastname: Wang
authors.forename: Lin
authors.initials: L
authors.lastname: Peng
authors.forename: Fang
authors.initials: F
authors.lastname: Tian
authors.forename: Xiao-Ying
authors.initials: XY
authors.lastname: Xu
authors.forename: Li-Xin
authors.initials: LX
authors.lastname: Wang
mesh_terms: D000478:Alkylation; D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005663:Furans; D007211:Indoles; D013141:Spiro Compounds; C003422:tetronic acid