Highly Regioselective and Chemoselective [3 + 3] Annulation of Enaminones with ortho- Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N-Oxides

Xue-Bing Chen; Shun-Tao Huang; Jie Li; Qi Yang; Li Yang; Fuchao Yu

doi:10.1021/acs.orglett.1c00710

Highly Regioselective and Chemoselective [3 + 3] Annulation of Enaminones with ortho- Fluoronitrobenzenenes: Divergent Synthesis of Aposafranones and Their N-Oxides

Org Lett. 2021 Apr 16;23(8):3032-3037. doi: 10.1021/acs.orglett.1c00710. Epub 2021 Apr 1.

Authors

Xue-Bing Chen¹, Shun-Tao Huang¹, Jie Li¹, Qi Yang¹, Li Yang¹, Fuchao Yu²

Affiliations

¹ College of Science, Honghe University, Mengzi, 661199, Yunnan, China.
² Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650504, People's Republic of China.

PMID: 33792341
DOI: 10.1021/acs.orglett.1c00710

Abstract

A base-promoted unprecedented strategy for the regioselective and chemoselective divergent synthesis of highly functionalized aposafranones and their N-oxides has been developed from the [3 + 3] annulation of enaminones with o-fluoronitrobenzenenes. This novel synthetic strategy offers an alternative method for the construction of aposafranones and their N-oxides are meaningful in the fields of both biology and organic synthesis. The established protocol explores the annulation scope of enaminones, and it expands the application of nitro-based cyclization.

Publication types

Research Support, Non-U.S. Gov't