Ring-opening of 2,3-epoxy-1-propanol with R3Al: Unprecedented regiochemical switching simply achieved by changing alkyl substituents of aluminium reagent |
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| Authors: | Janusz Lewiński Pawe? Horeglad Iwona Justyniak Zbigniew Ochal |
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| Affiliation: | a Department of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
b Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland |
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| Abstract: | Several control experiments were designed to optimize the reaction of 2,3-epoxy-1-propanol with R3Al (R = Me, Et or iBu) and to probe for the nature of aluminium-bound alkyl groups that influence the reactivity and selectivity. The reported studies revealed that the Et3Al mediated reaction leads to the C-2 product in contrast to the well-known C-3 substitution promoted by Me3Al. |
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| Keywords: | Aluminum Regioselectivity Epoxides Alkylation |
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