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1,3-Dipolar cycloadditions of new 2,5-bifunctionalized 5-membered cyclic nitrones

Basic information
Original title:1,3-Dipolar cycloadditions of new 2,5-bifunctionalized 5-membered cyclic nitrones
Authors:Marian Buchlovič, Simona Hebanová, Milan Potáček
Further information
Citation:BUCHLOVIČ, Marian, Simona HEBANOVÁ a Milan POTÁČEK. 1,3-Dipolar cycloadditions of new 2,5-bifunctionalized 5-membered cyclic nitrones. Tetrahedron, Oxford, England: Pergamon - Elsevier Science, 2012, roč. 68, č. 14, s. 3117-3122. ISSN 0040-4020. doi:10.1016/j.tet.2012.01.043.Export BibTeX
@article{977506,
author = {Buchlovič, Marian and Hebanová, Simona and Potáček, Milan},
article_location = {Oxford, England},
article_number = {14},
doi = {http://dx.doi.org/10.1016/j.tet.2012.01.043},
keywords = {Cyclic nitrones; 1-3-Dipolar cycloadditions; Stereoselectives reactions; Dipolarophile; Nitrone complexes},
language = {eng},
issn = {0040-4020},
journal = {Tetrahedron},
title = {1,3-Dipolar cycloadditions of new 2,5-bifunctionalized 5-membered cyclic nitrones},
volume = {68},
year = {2012}
}
Original language:English
Field:Organic chemistry
Type:Article in Periodical
Keywords:Cyclic nitrones; 1-3-Dipolar cycloadditions; Stereoselectives reactions; Dipolarophile; Nitrone complexes

A new family of 5-membered cyclic nitrones bearing functional groups at positions 2,5 were tested in 1,3-cycloadditions with various dipolarophiles. Studied reactions offered corresponding cycloaducts as single diastereomers in high yields. The reaction scope was examined, 23 compounds were isolated and fully characterized. The comparison of the reactivity was done by a study of reaction conversions while different nitrones or dipolarophiles were used. In addition, we have studied the exceptional reactivity of nitrone bearing benzylamino group in position 2. The formation of nitrone complex and evaluation of its reactivity in 1,3-DC is presented.

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