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.; M. SPISAKOVA; M. BABJAK; J. DOHANOSOVA; Jaromír MAREK ; J. MONCOL a R. FISCHER

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

https://doi.org/10.1002/ejoc.201601488

UT WoS

000394901700008

EID Scopus

2-s2.0-85013128239

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://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 = {https://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://doi.org/10.1002/ejoc.201601488.

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