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2019-07-01

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/143377

Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines

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https://doi.org/10.1002/adsc.201900372

Abstract

In the presence of 3-5 mol% Crabtree's catalyst or the corresponding tetrakis[3,5-bis(trifluoromethyl)phenyl]borate salt (Cy3P)Ir+(pyridine)(1,5-cyclooctadiene)·X- {X = PF6, [3,5-(F3C)2C6H3]4B}, aryl 1,1-disubstituted epoxides such as α-methylstyrene oxide underwent chemoselective isomerization to aldehydes; treatment with benzhydrylamine and pyrrolidine and redn. with NaBH4 yielded 2,2-disubstituted amines such as PhCHMeCH2NHR [R = Ph2CH, 4-MeOC6H4, PhCH2, (R)-PhCHMe] in one pot. DFT calcns. were performed to rationalize the obsd. selectivity.

Subject

Iridi, Isomerització

Subject (English)

Iridium, Isomerization

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Articles publicats en revistes (Química Inorgànica i Orgànica)

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CABRÉ MONTESINOS, Albert, et al. Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines. Advanced Synthesis & Catalysis. 2019. Vol. 361, num. 15, pags. 3624-3631. ISSN 1615-4150. [consulted: 14 of August of 2026]. Available at: https://hdl.handle.net/2445/143377

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