Phosphine-catalyzed [3 + 2] annulation of 2-aminoacrylates with allenoates and mechanistic studies. Issue 12 (27th May 2020)

• Record Type: Journal Article
• Authors: Wu, Xiao-Yun; Gui, Hou-Ze; Jangra, Harish; Wei, Yin; Zipse, Hendrik; Shi, Min
• Is Part Of: Catalysis science & technology. Volume 10:Issue 12(2020)
• Page Start: 3959
• Page End: 3964
• Publication Date: 2020-05-27
• Subjects: Catalysis -- Periodicals; 541.395
• DOI: 10.1039/d0cy00092b
• Languages: English
• ISSNs: 2044-4753

Abstract

Abstract : A phosphine catalyzed formal [3 + 2] annulation was disclosed, affording 3-pyrrolines containing an amino quaternary stereogenic center in good to excellent yields. The catalytic mechanism was investigated by DFT and kinetic studies. Abstract : A convenient and efficient strategy for the synthesis of 3-pyrrolines containing an amino quaternary stereogenic center via phosphine-catalyzed formal [3 + 2] annulation of 2-aminoacrylates with allenoates is disclosed. A wide range of substrates underwent this reaction smoothly, affording a series of 3-pyrrolines in good to excellent yields, and it could be extended to a gram-scale reaction. The kinetic profiles and the calculated methyl anion affinity (MAA) values were employed to explain the reactivities of different allenoates used in the reaction, which provides deep understanding for the catalytic mechanism of this type of reaction.