Silver-catalyzed cyclization of α-imino-oxy acids to fused tetralone derivatives

Kai Liu; Feng Li; Jingjing Wang; Zhaowei Zhang; Fengge Du; Hanxiao Su; Yonghong Wang; Qingqing Yuan; Fei Li; Teng Wang

doi:10.1039/D2OB02329F

Silver-catalyzed cyclization of α-imino-oxy acids to fused tetralone derivatives†

Kai Liu,^a Feng Li,

*^bc Jingjing Wang,^bc Zhaowei Zhang,^c Fengge Du,^c Hanxiao Su,^c Yonghong Wang,^c Qingqing Yuan,^c Fei Li*^a and Teng Wang*^d

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* Corresponding authors

^a School of Petrochemical Engineering, Liaoning Petrochemical University, Fushun 113001, China
E-mail: lnpulf@126.com

^b College of Food Science and Pharmaceutical Engineering, Zaozhuang University, Zaozhuang 277160, China
E-mail: lifeng20150720@163.com

^c College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, China

^d School of Chemistry, Beihang University, Beijing, China
E-mail: tengwang@buaa.edu.cn

Abstract

A silver-catalyzed intramolecular radical relay cyclization of α-imino-oxy acids under mild conditions has been described. This reaction offers facile access to a diverse range of fused tetralone derivatives with exquisite stereoselectivity in moderate to good yields (40–98%). Experimental studies show that the reaction undergoes a decarboxylation and acetone fragmentation/1,5-hydrogen atom transfer (HAT)/cyclization process.

Organic & Biomolecular Chemistry

Silver-catalyzed cyclization of α-imino-oxy acids to fused tetralone derivatives†

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Silver-catalyzed cyclization of α-imino-oxy acids to fused tetralone derivatives

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