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@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.
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