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Lewis Acid Catalyzed Electrophilic Aminomethyloxygenative Cyclization of Alkynols with <i>N</i>,<i>O</i>-Aminals

Anrong Chen, Houjian Yu, Jiaqi Yan, Hanmin Huang

2020Organic Letters21 citationsDOI

Abstract

-aminals. The new process proceeds efficiently under very mild conditions via a pathway that is opposite to classical carbo-metalation. These reactions exhibit broad substrate generality and functional group compatibility, leading to a wide variety of 5-8-membered oxacycles bearing diverse functional groups. The cyclization products can be elaborated via simple functional group transformations to generate synthetically useful oxacycles.

Topics & Concepts

ChemistryCatalysisElectrophileLewis acids and basesMedicinal chemistryOrganic chemistryStereochemistryCombinatorial chemistryCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCyclopropane Reaction Mechanisms