Chemoselective Oxidation of Isoxazolidines with Ruthenium Tetroxide: A Successful Intertwining of Combined Theoretical and Experimental Data

Autor:	Laura Legnani, Salvatore V. Giofré, Daniela Iannazzo, Consuelo Celesti, Lucia Veltri, Maria Assunta Chiacchio
Jazyk:	angličtina
Rok vydání:	2022
Předmět:	ruthenium tetroxide oxidation DFT calculations 3-isoxazolidinone chemoselectivity Organic chemistry QD241-441
Zdroj:	Molecules, Vol 27, Iss 17, p 5390 (2022)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules27175390
Popis:	The direct oxidation reaction of isoxazolidines plays an important role in organic chemistry, leading to the synthesis of biologically active compounds. In this paper, we report a computational mechanistic study of RuO4-catalyzed oxidation of differently N-substituted isoxazolidines 1a–c. Attention was focused on the endo/exo oxidation selectivity. For all the investigated compounds, the exo attack is preferred to the endo one, showing exo percentages growing in parallel with the stability order of transient carbocations found along the reaction pathway. The study has been supported by experimental data that nicely confirm the modeling results.
Databáze:	Directory of Open Access Journals
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