title: Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones withN-itaconimides.
abstract: A dipeptide-based urea-amide tertiary amine (DP-UAA) was shown to be an effective Brønsted base catalyst for the first asymmetric annulation reaction between 5H-thiazol-4-ones andN-itaconimides. High levels of enantioselectivity (up to 99% ee) and diastereoselectivity (>19:1 dr) were obtained for a series of spirocyclic 1,4-sulfur-bridged piperidinone-based succinimides.
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, 475004, Henan, P. R. China.
authors.forename: Shuai
authors.initials: S
authors.lastname: Qiu
authors.affiliation: Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, 637371, Singapore.
authors.forename: Choon-Hong
authors.initials: CH
authors.lastname: Tan
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, 475004, Henan, P. R. China.
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Jiang
keywords: 5H-thiazol-4-ones; N-itaconimides; [4 + 2] annulation; asymmetric organocatalysis; dipeptide-based Brønsted bases