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Enantioselective Copper-Catalyzed Electrophilic Dearomative Azidation of β-Naphthols.

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The first example of copper-catalyzed enantioselective dearomative azidation of β-naphthols using a readily available N3-transfer reagent is reported. A series of 2-hydroxy-1-naphthamides bearing a complex N-substituent were converted to the… Click to show full abstract

The first example of copper-catalyzed enantioselective dearomative azidation of β-naphthols using a readily available N3-transfer reagent is reported. A series of 2-hydroxy-1-naphthamides bearing a complex N-substituent were converted to the corresponding products in high yields with up to 96% ee, and chiral 1-azido-2-hydroxy-1-naphthoates were obtained with up to 90% ee under mild reaction conditions. The azides could be further transformed into the corresponding 1,2,3-triazoles smoothly via "click" reaction.

Keywords: dearomative azidation; enantioselective copper; azidation naphthols; copper catalyzed

Journal Title: Organic letters
Year Published: 2019

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