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

doi:10.1007/s40242-016-5495-x

Abstract

Abstract:

Phosphine-catalyzed [4+2] annulations of 2-(acetoxymethyl)buta-2,3-dienoates with α-aminonitriles have been developed, in which α-aminonitriles serve as C, N-bisnucleophilic reaction partners and 2-(acetoxymethyl)buta- 2,3-dienoates as "C4 synthons" respectively. A number of α-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.

Key words: Annulation, Catalysis, Tetrahydropyridine

JANG Hochol, LIU Wei, ZHANG SEAN Xiao'an, LIAO Weiwei. Phosphine-catalyzed [4+2] Annulations of α-Aminonitriles with Allenoates: Synthesis of Functionalized Tetrahydropyridines[J]. Chemical Research in Chinese Universities, 2016, 32(3): 385-389.

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