Reversal of Stereoselectivity in Cycloadditions of
Five-Membered Cyclic Nitrones Derived from Hexoses

J 2017

Reversal of Stereoselectivity in Cycloadditions of Five-Membered Cyclic Nitrones Derived from Hexoses

MALATINSKY, T., M. SPISAKOVA, M. BABJAK, J. DOHANOSOVA, Jaromír MAREK et. al.

Základní údaje

Originální název

Reversal of Stereoselectivity in Cycloadditions of Five-Membered Cyclic Nitrones Derived from Hexoses

Autoři

MALATINSKY, T. (703 Slovensko), M. SPISAKOVA (703 Slovensko), M. BABJAK (703 Slovensko), J. DOHANOSOVA (703 Slovensko), Jaromír MAREK (203 Česká republika, garant, domácí), J. MONCOL (703 Slovensko) a R. FISCHER (703 Slovensko)

Vydání

European Journal of Organic Chemistry, Weinheim, WILEY-VCH, 2017, 1434-193X

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 2.882

Kód RIV

RIV/00216224:14740/17:00100421

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1002/ejoc.201601488

UT WoS

000394901700008

Klíčová slova anglicky

Heterocycles; Nitrones; Carbohydrates; Cycloaddition; Diastereoselectivity

Štítky

CF SAXS, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 19. 3. 2018 14:26, Mgr. Pavla Foltynová, Ph.D.

Anotace

V originále

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.

Návaznosti

LM2015043, projekt VaV

Název: Česká infrastruktura pro integrativní strukturní biologii (Akronym: CIISB)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Czech Infrastructure for Integrative Structural Biology

Citovat

MALATINSKY, T., M. SPISAKOVA, M. BABJAK, J. DOHANOSOVA, Jaromír MAREK, J. MONCOL a R. FISCHER. Reversal of Stereoselectivity in Cycloadditions of Five-Membered Cyclic Nitrones Derived from Hexoses. European Journal of Organic Chemistry. Weinheim: WILEY-VCH, 2017, roč. 2018, č. 6, s. 1086-1098. ISSN 1434-193X. Dostupné z: https://dx.doi.org/10.1002/ejoc.201601488.

@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 a 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, roč.~2018, č.~6, s.~1086-1098. ISSN~1434-193X. Dostupné z: https://dx.doi.org/10.1002/ejoc.201601488.

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