Enantioselective organocatalytic cycloadditions for the
synthesis of medium-sized rings

J 2023

Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings

OTEVŘEL, Jan, Macarena EUGUI, Sebastijan RIČKO a Karl Anker JØRGENSEN

Základní údaje

Originální název

Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings

Autoři

OTEVŘEL, Jan (203 Česká republika, domácí), Macarena EUGUI (208 Dánsko), Sebastijan RIČKO (208 Dánsko) a Karl Anker JØRGENSEN (208 Dánsko, garant)

Vydání

Nature Synthesis, Nature Publishing Group, 2023, 2731-0582

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30104 Pharmacology and pharmacy

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Kód RIV

RIV/00216224:14160/23:00132475

Organizační jednotka

Farmaceutická fakulta

DOI

http://dx.doi.org/10.1038/s44160-023-00416-1

UT WoS

001124810900009

Klíčová slova anglicky

N-HETEROCYCLIC CARBENECATALYZED 3+4 ANNULATIONDIARYLPROLINOL SILYL ETHERSDIELS-ALDER REACTIONSNATURAL-PRODUCTSASYMMETRIC-SYNTHESISBRONSTED ACIDBOND DONORSENALSCONSTRUCTION

Štítky

rivok, ÚChL

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 5. 4. 2024 07:44, Mgr. Daniela Černá

Anotace

V originále

Optically active medium-sized cyclic compounds are often found in natural products and are therefore attractive targets in organic synthesis. However, generating these cyclic entities with specific stereochemistry is far from trivial owing to unfavourable entropic factors and competing pathways that favour the formation of rings of lesser size. As a result, conventional ring-forming strategies can be challenging, and alternative methods, such as organocatalytic cycloadditions, have emerged to address these issues. Enantioselective synthesis of medium-sized rings by organocatalytic cycloadditions is a rapidly growing field of research offering opportunities that are complementary to metal-catalysed cycloadditions. Several organocatalytic approaches are available, including enamine/iminium-ion activation, along with catalysis using Lewis and Brønsted acids, hydrogen-bond donors, N-heterocyclic carbenes, and nucleophilic phosphines and amines. Here we discuss the ability of organocatalytic cycloadditions to synthesize stereodefined medium-sized ring architectures, critically evaluate current synthetic strategies, and highlight avenues for further development.

Návaznosti

MUNI/A/1096/2022, interní kód MU

Název: Vývoj asymetrické Mannichovy reakce 2-sukcinimidyl, 2-glutarimidyl karboxylátů a příbuzných sloučenin

Investor: Masarykova univerzita, Vývoj asymetrické Mannichovy reakce 2-sukcinimidyl, 2-glutarimidyl karboxylátů a příbuzných sloučenin

Citovat

OTEVŘEL, Jan, Macarena EUGUI, Sebastijan RIČKO a Karl Anker JØRGENSEN. Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings. Nature Synthesis. Nature Publishing Group, 2023, roč. 2, č. 12, s. 1142-1158. ISSN 2731-0582. Dostupné z: https://dx.doi.org/10.1038/s44160-023-00416-1.

@article{2348497,
   author = {Otevřel, Jan and Eugui, Macarena and Ričko, Sebastijan and Jørgensen, Karl Anker},
   article_number = {12},
   doi = {http://dx.doi.org/10.1038/s44160-023-00416-1},
   keywords = {N-HETEROCYCLIC CARBENECATALYZED 3+4 ANNULATIONDIARYLPROLINOL SILYL ETHERSDIELS-ALDER REACTIONSNATURAL-PRODUCTSASYMMETRIC-SYNTHESISBRONSTED ACIDBOND DONORSENALSCONSTRUCTION},
   language = {eng},
   issn = {2731-0582},
   journal = {Nature Synthesis},
   title = {Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings},
   url = {https://www.nature.com/articles/s44160-023-00416-1},
   volume = {2},
   year = {2023}
}

TY  - JOUR
ID  - 2348497
AU  - Otevřel, Jan - Eugui, Macarena - Ričko, Sebastijan - Jørgensen, Karl Anker
PY  - 2023
TI  - Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings
JF  - Nature Synthesis
VL  - 2
IS  - 12
SP  - 1142-1158
EP  - 1142-1158
PB  - Nature Publishing Group
SN  - 27310582
KW  - N-HETEROCYCLIC CARBENECATALYZED 3+4 ANNULATIONDIARYLPROLINOL SILYL ETHERSDIELS-ALDER REACTIONSNATURAL-PRODUCTSASYMMETRIC-SYNTHESISBRONSTED ACIDBOND DONORSENALSCONSTRUCTION
UR  - https://www.nature.com/articles/s44160-023-00416-1
N2  - Optically active medium-sized cyclic compounds are often found in natural products and are therefore attractive targets in organic synthesis. However, generating these cyclic entities with specific stereochemistry is far from trivial owing to unfavourable entropic factors and competing pathways that favour the formation of rings of lesser size. As a result, conventional ring-forming strategies can be challenging, and alternative methods, such as organocatalytic cycloadditions, have emerged to address these issues. Enantioselective synthesis of medium-sized rings by organocatalytic cycloadditions is a rapidly growing field of research offering opportunities that are complementary to metal-catalysed cycloadditions. Several organocatalytic approaches are available, including enamine/iminium-ion activation, along with catalysis using Lewis and Brønsted acids, hydrogen-bond donors, N-heterocyclic carbenes, and nucleophilic phosphines and amines. Here we discuss the ability of organocatalytic cycloadditions to synthesize stereodefined medium-sized ring architectures, critically evaluate current synthetic strategies, and highlight avenues for further development.
ER  -

OTEVŘEL, Jan, Macarena EUGUI, Sebastijan RIČKO a Karl Anker JØRGENSEN. Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings. \textit{Nature Synthesis}. Nature Publishing Group, 2023, roč.~2, č.~12, s.~1142-1158. ISSN~2731-0582. Dostupné z: https://dx.doi.org/10.1038/s44160-023-00416-1.

Podrobný výpis o publikaci