Journal of Organic Chemistry p. 5492 - 5503 (2019)
Update date:2022-07-29
Topics: Phosphazene Superbase-Mediated Regio- and Stereoselective Iodoaminocyclization 2-(1-Alkynyl)benzamides Synthesis of Isoindolin-1-ones
Mehta, Saurabh
Brahmchari, Dhirendra
Phosphazene superbase P4-t-Bu mediated iodoaminocyclization of 2-(1-alkynyl)benzamides is reported. The reaction works under ambient conditions and instantaneously results in the synthesis of isoindolin-1-ones in 65-97% yields, in a regio- and stereoselective manner. The exclusive formation of products with Z-geometry (across the exo C?C bond) has been confirmed through X-ray crystallography. The methodology also provides an easy access to aristolactams, an important class of natural products. This has been successfully demonstrated by synthesizing two aristolactam derivatives (including Cepharanone B).
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