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Catalyst-free Cleavage of Amide and C-O Double Bond for the Diastereoselective Synthesis of Trifluoromethyl-Containing Dihydrooxazole Derivatives.

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A novel and efficient cascade method has been developed for the diastereoselective preparation of trifluoromethyl-containing dihydrooxazoles in high yields. The reaction was applicable to electron-deficient, electron-rich arenes, heteroarenes, and alkyl… Click to show full abstract

A novel and efficient cascade method has been developed for the diastereoselective preparation of trifluoromethyl-containing dihydrooxazoles in high yields. The reaction was applicable to electron-deficient, electron-rich arenes, heteroarenes, and alkyl groups. Control experiments were conducted to explore the reaction mechanism and reveal that the byproduct formed in situ is the catalyst for this reaction and a tether derived from trifluoropyruvate is a key intermediate for this reaction.

Keywords: cleavage amide; free cleavage; trifluoromethyl containing; reaction; trifluoromethyl; catalyst free

Journal Title: Organic letters
Year Published: 2019

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