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- W2892079739 abstract "The Crabtree’s reagent catalyzes the isomerization of N-sulfonyl 2,2-disubstituted aziridines to allyl amines. The selectivity of allyl amine vs imine is very high (up to 99/1). The unprecedented isomerization takes place in mild conditions without activation of the catalyst by hydrogen. The mechanism has been studied computationally by DFT calculations; instead of the usual hydrogenation of COD, the catalytic species is formed by a loss of the pyridine ligand. Approaching of aziridine to this unsaturated species leads to a carbocation intermediate through a low energy barrier. A metal-mediated tautomerization involving sequentially γ-H elimination and N–H reductive elimination affords selectively the allyl amine. The readiness of the CγH bond to participate in the H elimination step accounts for the selectivity toward the allyl amine product." @default.
- W2892079739 created "2018-09-27" @default.
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- W2892079739 date "2018-09-06" @default.
- W2892079739 modified "2023-10-16" @default.
- W2892079739 title "Iridium-Catalyzed Isomerization of <i>N</i>-Sulfonyl Aziridines to Allyl Amines" @default.
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- W2892079739 doi "https://doi.org/10.1021/acs.orglett.8b02450" @default.
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