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Iridium-catalyzed regiospecific and stereospecific allylic amination for the syntheses of α,β-unsaturated γ-amino esters and the bifurcation of the reaction pathway leading to the formation of oxazolidin-2-ones

Title
Iridium-catalyzed regiospecific and stereospecific allylic amination for the syntheses of α,β-unsaturated γ-amino esters and the bifurcation of the reaction pathway leading to the formation of oxazolidin-2-ones
Authors
Lee J.H.Lee S.-G.
Ewha Authors
이상기이준희
SCOPUS Author ID
이상기scopus
Issue Date
2013
Journal Title
Chemical Science
ISSN
2041-6520JCR Link
Citation
vol. 4, no. 7, pp. 2922 - 2927
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
A pair of iridium-catalyzed regiospecific and stereospecific reactions of the carbonates of γ-hydroxy α,β-unsaturated esters were developed. The reaction pathways are strongly affected by the choice of amines employed. A diverse range of γ-substituted α,β-unsaturated γ-amino esters were prepared in excellent yields with various amine nucleophiles such as benzylamine, diallylamine, morpholine, aniline and N-methylaniline. Substitution at the γ-position was well tolerated, encompassing alkyl, aryl and heteroaryl substituents. Enantioenriched (E)-α,β-unsaturated γ-amino esters could also be synthesized from the corresponding enantioenriched allylic carbonates with complete chirality transfer. In sharp contrast, a series of 3,4-disubstituted oxazolidin-2-ones were obtained by using allylamine as a nucleophile. © 2013 The Royal Society of Chemistry.
DOI
10.1039/c3sc50901j
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자연과학대학 > 화학·나노과학전공 > Journal papers
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