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@article{1411802,
author = {Malatinsky, T. and Spisakova, M. and Babjak, M. and Dohanosova, J. and Marek, Jaromír and Moncol, J. and Fischer, R.},
article_location = {Weinheim},
article_number = {6},
doi = {http://dx.doi.org/10.1002/ejoc.201601488},
keywords = {Heterocycles; Nitrones; Carbohydrates; Cycloaddition; Diastereoselectivity},
language = {eng},
issn = {1434-193X},
journal = {European Journal of Organic Chemistry},
title = {Reversal of Stereoselectivity in Cycloadditions of Five-Membered Cyclic Nitrones Derived from Hexoses},
url = {https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.201601488},
volume = {2018},
year = {2017}
}
TY - JOUR
ID - 1411802
AU - Malatinsky, T. - Spisakova, M. - Babjak, M. - Dohanosova, J. - Marek, Jaromír - Moncol, J. - Fischer, R.
PY - 2017
TI - Reversal of Stereoselectivity in Cycloadditions of Five-Membered Cyclic Nitrones Derived from Hexoses
JF - European Journal of Organic Chemistry
VL - 2018
IS - 6
SP - 1086-1098
EP - 1086-1098
PB - WILEY-VCH
SN - 1434193X
KW - Heterocycles
KW - Nitrones
KW - Carbohydrates
KW - Cycloaddition
KW - Diastereoselectivity
UR - https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.201601488
N2 - Two five-membered cyclic nitrones derived from hexoses, a newly synthesized D-allo-configured nitrone and an already known D-talo-configured nitrone, have been examined in 1,3-dipolar cycloaddition reactions with vinyl acetate, allyl benzoate, methyl acrylate, acrylonitrile, and vinylene carbonate. The reactions of the D-allo-configured nitrone proceeded preferentially through the expected exo-anti transition state, but all the cycloadditions of the D-talo-configured nitrone surprisingly showed high exo-syn selectivity. This reversal of stereoselectivity has been explained by 3D analysis of the preferred conformations of the nitrones, obtained from X-ray data. The structures were further inspected using CONFLEX, PM5, and DFT calculations. All these methods revealed that the dioxolane substituents attached to C-5 of both nitrones had opposite spatial locations.
ER -
MALATINSKY, T., M. SPISAKOVA, M. BABJAK, J. DOHANOSOVA, Jaromír MAREK, J. MONCOL and R. FISCHER. Reversal of Stereoselectivity in Cycloadditions of Five-Membered Cyclic Nitrones Derived from Hexoses. \textit{European Journal of Organic Chemistry}. Weinheim: WILEY-VCH, 2017, vol.~2018, No~6, p.~1086-1098. ISSN~1434-193X. Available from: https://dx.doi.org/10.1002/ejoc.201601488.
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