jo9b00246_si_002.cif (763.73 kB)
Lewis Acids Promoted 3 + 2 Cycloaddition of Oxaziridines and Cyclic Allylic Alcohols through Carbonyl Imine Intermediates
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posted on 2019-03-14, 00:00 authored by Erbao Zhao, Feilong Zhou, Yujun ZhaoSyntheses of isoxazolidines through
the carbonyl imine intermediates
are currently limited to monosubstituted olefin substrates. Herein,
we reported syntheses of novel bicyclic isoxazolidine-containing compounds
through 1,3-dipolar cycloaddition reactions using cyclic allylic alcohols
as substrates, which proved challenging in previous reports. Generally,
the reaction yields range from good to high, and the reaction substrates
tolerate various functional groups, including the cyclopropyl and
amine groups. Mechanistic studies suggest that an allylic cation and
a carbonyl imine intermediate are involved and responsible for the
observed stereochemistry and diastereoselectivity.
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carbonyl imine intermediatesCarbonyl Imine Intermediates Synthesesreaction substrates2 CycloadditionCyclic Allylic Alcoholsmonosubstituted olefin substratesMechanistic studiescyclic allylic alcoholsallylic cationcarbonyl iminereaction yields rangenovel bicyclic isoxazolidine-containing compoundsLewis Acids Promoted 3amine groups
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