Phosphine-catalyzed [3+2] annulation of 2-aminoacrylates with allenoates and mechanistic studies

Wu, Xiao-Yun; Gui, Hou-Ze; Jangra, Harish; Wei, Yin; Zipse, Hendrik and Shi, Min (2020): Phosphine-catalyzed [3+2] annulation of 2-aminoacrylates with allenoates and mechanistic studies. In: Catalysis Science & Technology, Vol. 10, No. 12: pp. 3959-3964

Abstract

A convenient and efficient strategy for the synthesis of 3-pyrrolines containing an amino quaternary stereogenic centerviaphosphine-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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 2044-4753
• Language: English