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 and Karl Anker JØRGENSEN

Basic information

Original name

Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings

Authors

OTEVŘEL, Jan (203 Czech Republic, belonging to the institution), Macarena EUGUI (208 Denmark), Sebastijan RIČKO (208 Denmark) and Karl Anker JØRGENSEN (208 Denmark, guarantor)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

RIV identification code

RIV/00216224:14160/23:00132475

Organization unit

Faculty of Pharmacy

DOI

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

UT WoS

001124810900009

Keywords in English

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

Abstract

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.

Links

MUNI/A/1096/2022, interní kód MU

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

Investor: Masaryk University

Citovat

OTEVŘEL, Jan, Macarena EUGUI, Sebastijan RIČKO and Karl Anker JØRGENSEN. Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings. Nature Synthesis. Nature Publishing Group, 2023, vol. 2, No 12, p. 1142-1158. ISSN 2731-0582. Available from: 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 and Karl Anker JØRGENSEN. Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings. \textit{Nature Synthesis}. Nature Publishing Group, 2023, vol.~2, No~12, p.~1142-1158. ISSN~2731-0582. Available from: https://dx.doi.org/10.1038/s44160-023-00416-1.

Detailed Information on Publication Record