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Reactions of 5-Aminoisoxazoles with α-Diazocarbonyl Compounds: Wolff Rearrangement vs N–H Insertion

Author:
Ge, Yun, Sun, Wangbin, Chen, Yang, Huang, Yulin, Liu, Zhuang, Jiang, Yaojia, Loh, Teck-Peng
Source:
Journal of organic chemistry 2019 v.84 no.5 pp. 2676-2688
ISSN:
1520-6904
Subject:
amides, amino acids, chemical reactions, chemical structure, chemoselectivity, organic chemistry
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 Rh₂(Oct)₄. Both reactions proceed under mild reaction conditions and feature a broad substrate scope.
Agid:
6323048