4.8 Article

Rh-Catalyzed [4+2] Annulation with a Removable Monodentate Structure toward Iminopyranes and Pyranones by C-H Annulation

Journal

ORGANIC LETTERS
Volume 24, Issue 16, Pages 3003-3008

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00912

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Funding

  1. National Natural Science Foundation of China [22161022]
  2. Natural Science Foundation of Jiangxi Province [20202ACBL203006]

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The Rh-catalyzed reactions of N-pyridinyl enaminones with internal alkynes leading to the synthesis of iminopyranes via C-H bond activation and subsequent tautomeric O-H bond cleavage are reported. The pyridine ring in the amino group acts as an auxiliary monodentate site and can be easily removed by hydrolysis to afford pyranones.
The Rh-catalyzed reactions of N-pyridinyl enaminones with internal alkynes leading to the synthesis of iminopyranes via a key C-H bond activation and subsequent tautomeric O-H bond cleavage are reported. Moreover, the pyridine ring in the amino group acts as an auxiliary monodentate site for this annulation and can be easily removed by a simple hydrolysis to afford pyranones.

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