4.8 Article

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

Journal

ORGANIC LETTERS
Volume 23, Issue 8, Pages 3032-3037

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00710

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Funding

  1. National Natural Science Foundation of China [21961018]
  2. Program for Innovative Research Team (in Science and Technology) in University of Yunnan Province

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This novel synthetic strategy uses base-catalyzed annulation to selectively generate highly functionalized aposafranones and their N-oxides, offering a new method in organic synthesis and biology.
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.

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