Phosphine-catalyzed [4＋2] Annulations of α-Aminonitriles with Allenoates： Synthesis of Functionalized Tetrahydropyridines

• Published in: Chemical research in Chinese universities Vol. 32; no. 3; pp. 385 - 389
• Main Authors: Jang, Hochol, Liu, Wei, Zhang Sean, Xiao’an, Liao, Weiwei
• Format: Journal Article
• Language: English
• Published: Changchun Jilin University and The Editorial Department of Chemical Research in Chinese Universities 01.06.2016
• Subjects: Analytical Chemistry; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Inorganic Chemistry; Organic Chemistry; Physical Chemistry; α-氨基腈; 三苯基膦; 丙二烯; 乙酰氧基; 催化剂; 合成子; 四氢嘧啶; 官能化; Tetrahydropyridine; Annulation; Catalysis
• ISSN: 1005-9040; 2210-3171
• DOI: 10.1007/s40242-016-5495-x

Phosphine-catalyzed [4＋2] annulations of 2-（acetoxymethyl）buta-2,3-dienoates with α-aminonitriles have been developed, in which a-aminonitriles serve as C, N-bisnucleophilic reaction partners and 2-（acetoxymethyl）buta- 2,3-dienoates as ＂C4 synthons＂ respectively. A number of a-aminonitriles could be successfully applied to giving multifunctional desired products using PPh3 as catalyst. This method provides a facile entry to access polysubstituted tetrahydropyridines bearing quaternary carbon centers. The possible reaction mechanism was also proposed.