Literature DB >> 12027644

Dicobalt octacarbonyl promoted rearrangement of 4-isoxazolines to acylaziridines: dramatic rate acceleration with very high substrate tolerance.

Teruhiko Ishikawa1, Takayuki Kudoh, Juri Yoshida, Ayako Yasuhara, Shinobu Manabe, Seiki Saito.   

Abstract

[reaction: see text] Dicobalt octacarbonyl [Co(2)(CO)(8)] in acetonitrile at 75 degrees C triggers the cleavage of the N-O bond of 4-isoxazolines (1) to bring about the valence rearrangement to 2-acylaziridines (2). The isoxazolines were stable at 75 degrees C in the absence of the cobalt complex.

Entities:  

Year:  2002        PMID: 12027644     DOI: 10.1021/ol025906j

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Development of a concise synthesis of (-)-oseltamivir (Tamiflu).

Authors:  Barry M Trost; Ting Zhang
Journal:  Chemistry       Date:  2011-03-01       Impact factor: 5.236

Review 2.  Non-Aziridination Approaches to 3-Arylaziridine-2-carboxylic Acid Derivatives and 3-Aryl-(aziridin-2-yl)ketones.

Authors:  Boriss Strumfs; Kirils Velikijs; Romans Uljanovs; Stanislavs Sinkarevs; Ilze Strumfa
Journal:  Int J Mol Sci       Date:  2022-05-25       Impact factor: 6.208

3.  A Torquoselective Extrusion of Isoxazoline N-Oxides. Application to the Synthesis of Aryl Vinyl and Divinyl Ketones for Nazarov Cyclization.

Authors:  Daniel P Canterbury; Ildiko R Herrick; Joann Um; K N Houk; Alison J Frontier
Journal:  Tetrahedron       Date:  2009-04-18       Impact factor: 2.457

4.  Synthesis of spirocyclic Δ4-isoxazolines via [3 + 2] cycloaddition of indanone-derived ketonitrones with alkynes.

Authors:  Yilin Liu; Jiaxue Liu; Yan-Yun Liu; Boxiao Tang; Hongwei Lin; Yuanxiang Li; Lin Zhang
Journal:  RSC Adv       Date:  2021-09-13       Impact factor: 3.361

  4 in total

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