title: Asymmetric [3 + 2] Cycloaddition of 3-Amino Oxindole-Based Azomethine Ylides and α,β-Enones with Divergent Diastereocontrol on the Spiro[pyrrolidine-oxindoles].
abstract: A general and practical organocatalytic asymmetric 1,3-dipolar cycloaddition of 3-amino oxindole-based azomethine ylides and α,β-enones has been developed. This reaction delivered spiro[pyrrolidine-2,3'-oxindole] products in high yields with excellent regio- and enantioselectivities (up to 99% yield, >20:1 rr, 99% ee). In addition, an array of spiro[dihydropyrrole-2,3'-oxindoles] were readily accessed by oxidative dehydrogenation. Notably, the inversion of the diastereoselectivity of the spiro[pyrrolidine-oxindole] product could be easily achieved through a facile oxidation-reduction process.
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Guodong
authors.initials: G
authors.lastname: Zhu
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Qian
authors.initials: Q
authors.lastname: Wei
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Hongbo
authors.initials: H
authors.lastname: Chen
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Yanpeng
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Wen
authors.initials: W
authors.lastname: Shen
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Jingping
authors.identifier: 0000-0002-7576-0798
authors.initials: J
authors.lastname: Qu
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Baomin
authors.identifier: 0000-0001-9058-4983
authors.initials: B
authors.lastname: Wang