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https://hdl.handle.net/10356/147448
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. https://dx.doi.org/10.1021/acs.joc.8b02986 | 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. | URI: | https://hdl.handle.net/10356/147448 | ISSN: | 0022-3263 | DOI: | 10.1021/acs.joc.8b02986 | Schools: | School of Physical and Mathematical Sciences | 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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