Facile rearrangements of a vinylogous
alpha-hydroxy-beta-dicarbonyl substrate involving an apparent
oxirane C-C bond scission

J 2015

Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission

KUČERA, Roman, Ondřej HYLSE, Michal BABIAK a Jakub ŠVENDA

Základní údaje

Originální název

Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission

Autoři

KUČERA, Roman (703 Slovensko, domácí), Ondřej HYLSE (203 Česká republika, domácí), Michal BABIAK (703 Slovensko, domácí) a Jakub ŠVENDA (203 Česká republika, garant, domácí)

Vydání

Tetrahedron Letters, OXFORD, Pergamon Press, 2015, 0040-4039

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 2.347

Kód RIV

RIV/00216224:14310/15:00088775

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1016/j.tetlet.2015.09.015

UT WoS

000363828500002

Klíčová slova anglicky

Oxirane cleavage; Vinylogous rearrangement; Ring expansion; Ring contraction; Organic synthesis

Štítky

AKR, rivok

Změněno: 17. 4. 2017 10:55, Ing. Andrea Mikešková

Anotace

V originále

alpha-Hydroxy-beta-dicarbonyls are known to undergo base-induced rearrangement to alpha-acyloxy carbonyls by a mechanism believed to involve an oxirane C-C bond scission step. Herein, we report the first example of this process in a vinylogous system. An attempt to access the protected form of the putative oxirane intermediate revealed an additional rearrangement pathway that was available to the substrate. Oxirane C-C bond cleavage mechanisms were invoked to explain both isomerizations. (C) 2015 Elsevier Ltd. All rights reserved.

Návaznosti

GJ15-10504Y, projekt VaV

Název: Příprava unikátních modulátorů adenylyl cyklázy

Investor: Grantová agentura ČR, Příprava unikátních modulátorů adenylyl cyklázy

Citovat

KUČERA, Roman, Ondřej HYLSE, Michal BABIAK a Jakub ŠVENDA. Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission. Tetrahedron Letters. OXFORD: Pergamon Press, 2015, roč. 56, č. 45, s. 6171-6173. ISSN 0040-4039. Dostupné z: https://dx.doi.org/10.1016/j.tetlet.2015.09.015.

@article{1375990,
   author = {Kučera, Roman and Hylse, Ondřej and Babiak, Michal and Švenda, Jakub},
   article_location = {OXFORD},
   article_number = {45},
   doi = {http://dx.doi.org/10.1016/j.tetlet.2015.09.015},
   keywords = {Oxirane cleavage; Vinylogous rearrangement; Ring expansion; Ring contraction; Organic synthesis},
   language = {eng},
   issn = {0040-4039},
   journal = {Tetrahedron Letters},
   title = {Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission},
   url = {http://www.sciencedirect.com/science/article/pii/S0040403915300575},
   volume = {56},
   year = {2015}
}

TY  - JOUR
ID  - 1375990
AU  - Kučera, Roman - Hylse, Ondřej - Babiak, Michal - Švenda, Jakub
PY  - 2015
TI  - Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission
JF  - Tetrahedron Letters
VL  - 56
IS  - 45
SP  - 6171-6173
EP  - 6171-6173
PB  - Pergamon Press
SN  - 00404039
KW  - Oxirane cleavage
KW  - Vinylogous rearrangement
KW  - Ring expansion
KW  - Ring contraction
KW  - Organic synthesis
UR  - http://www.sciencedirect.com/science/article/pii/S0040403915300575
L2  - http://www.sciencedirect.com/science/article/pii/S0040403915300575
N2  - alpha-Hydroxy-beta-dicarbonyls are known to undergo base-induced rearrangement to alpha-acyloxy carbonyls by a mechanism believed to involve an oxirane C-C bond scission step. Herein, we report the first example of this process in a vinylogous system. An attempt to access the protected form of the putative oxirane intermediate revealed an additional rearrangement pathway that was available to the substrate. Oxirane C-C bond cleavage mechanisms were invoked to explain both isomerizations. (C) 2015 Elsevier Ltd. All rights reserved.
ER  -

KUČERA, Roman, Ondřej HYLSE, Michal BABIAK a Jakub ŠVENDA. Facile rearrangements of a vinylogous alpha-hydroxy-beta-dicarbonyl substrate involving an apparent oxirane C-C bond scission. \textit{Tetrahedron Letters}. OXFORD: Pergamon Press, 2015, roč.~56, č.~45, s.~6171-6173. ISSN~0040-4039. Dostupné z: https://dx.doi.org/10.1016/j.tetlet.2015.09.015.

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