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

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

Wang, Chong-Ji;Sun, Jian;Zhou, Wei;Xue, Jing;Ren, Bing-Tao;Zhang, Guang-Yi;Mei, Yan-Le;Deng, Qing-Hai;
Organic letters 2019 Vol. 21 pp. 7315-7319
320
wang2019enantioselectiveorganic

Abstract

The first example of copper-catalyzed enantioselective dearomative azidation of β-naphthols using a readily available N-transfer reagent is reported. A series of 2-hydroxy-1-naphthamides bearing a complex -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.

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