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氟代硝基苯与烯胺酮的高区域和化学选择性[3 + 3]环加成:阿朴色酮及其 -氧化物的发散合成。

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

机构信息

College of Science, Honghe University, Mengzi, 661199, Yunnan, China.

Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650504, People's Republic of China.

出版信息

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

Abstract

A base-promoted unprecedented strategy for the regioselective and chemoselective divergent synthesis of highly functionalized aposafranones and their -oxides has been developed from the [3 + 3] annulation of enaminones with -fluoronitrobenzenenes. This novel synthetic strategy offers an alternative method for the construction of aposafranones and their -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.

摘要

已开发出一种基于碱促进的前所未有的策略,用于从烯胺酮与 - 氟硝基苯的[3 + 3]环加成反应中,对高度官能化的阿朴色酮及其 - 氧化物进行区域选择性和化学选择性的发散合成。这种新颖的合成策略为阿朴色酮及其 - 氧化物的构建提供了一种替代方法,它们在生物学和有机合成领域都具有重要意义。所建立的方案探索了烯胺酮的环加成范围,并扩展了基于硝基的环化反应的应用。

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