Abstract
A highly chemoselective reaction between 5-aminoisoxazoles and α-diazocarbonyl compounds has been described. Both Wolff rearrangement and N-H insertion products can be obtained selectively by the judicious choice of reaction conditions. In the case of the Wolff rearrangement reactions, the N-isoxazole amides are accessed as the sole products under thermal conditions. On the other hand, α-amino acid derivatives of N-isoxazolescan be obtained through N-H insertion reactions in the presence of catalytic Rh 2 (Oct) 4 . Both reactions proceed under mild reaction conditions and feature a broad substrate scope.
Original language | English |
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Pages (from-to) | 2676-2688 |
Number of pages | 13 |
Journal | Journal of Organic Chemistry |
Volume | 84 |
Issue number | 5 |
DOIs | |
State | Published - 1 Mar 2019 |