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Tunable Key [3 + 2] and [2 + 1] Cycloaddition of Enaminones and α-Diazo Compounds for the Synthesis of Isomeric Isoxazoles: Metal-Controlled Selectivity.

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The three-component reactions of enaminones, α-diazo esters/ketones, and t-butyl nitrite (TBN) for the switchable synthesis of isomeric isoxazoles have been realized. The catalysis with Cu(II) salt provides 3,4-disubsituted isoxazoles via… Click to show full abstract

The three-component reactions of enaminones, α-diazo esters/ketones, and t-butyl nitrite (TBN) for the switchable synthesis of isomeric isoxazoles have been realized. The catalysis with Cu(II) salt provides 3,4-disubsituted isoxazoles via [3 + 2] cycloaddition. On the other hand, the catalysis of Ag(I) with identical substrates leads to isomeric isoxazoles with reversed C3 and C4 substitution based on a key [2 + 1] cycloaddition.

Keywords: key cycloaddition; synthesis isomeric; enaminones diazo; isomeric isoxazoles; cycloaddition

Journal Title: Organic letters
Year Published: 2023

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