Chemistry–A European Journal

Gold (I)??Catalyzed 6??endo??Dig Hydrative Cyclization of an Alkyne??Tethered Ynamide: Access to 1, 6??Dihydropyridin??2 (3H) ones

N Ghosh, S Nayak, AK Sahoo

Index: Ghosh, Nayan; Nayak, Sanatan; Sahoo, Akhila K. Chemistry - A European Journal, 2013 , vol. 19, # 29 p. 9428 - 9433

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Citation Number: 25

Abstract

Lewis acid promoted cyclization of π-tethered ynamide derivatives affords a diverse array of nitrogen-bearing heterocycles in a single-step.[1] The inherent polarization of the nitrogen lone-pair to the ynamide triple-bond under the influence of π-acids/Brønsted acids enhances the electrophilicity at the α-carbon to the nitrogen atom, which in turn propels regioselective attack of the nucleophile to a ketiniminium intermediate I (Scheme 1).[1] Thus, ...