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Title: Reactions of 5-aminoisoxazoles with α-diazocarbonyl compounds : wolff rearrangement vs N-H insertion
Authors: Ge, Yun
Sun, Wangbin
Chen, Yang
Huang, Yulin
Liu, Zhuang
Jiang, Yaojia
Loh, Teck-Peng
Keywords: Science::Chemistry
Issue Date: 2019
Source: Ge, Y., Sun, W., Chen, Y., Huang, Y., Liu, Z., Jiang, Y. & Loh, T. (2019). Reactions of 5-aminoisoxazoles with α-diazocarbonyl compounds : wolff rearrangement vs N-H insertion. The Journal of Organic Chemistry, 84(5), 2676-2688.
Journal: The Journal of 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.
ISSN: 0022-3263
DOI: 10.1021/acs.joc.8b02986
Rights: © 2019 American Chemical Society. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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