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Asymmetric transfer hydrogenation of cyclobutenediones [Elektronski vir]Lan, Shouang ...Four-membered carbocycles are fundamental substructures in bioactive molecules and approved drugs and serve as irreplaceable building blocks in organic synthesis. However, developing efficient ... protocols furnishing diversified four-membered ring compounds in a highly regio-, diastereo-, and enantioselective fashion remains challenging but very desirable. Here, we report the unprecedented asymmetric transfer hydrogenation of cyclobutenediones. The reaction can selectively afford three types of four-membered products in high yields with high stereoselectivities, and the highly functionalized products enable a series of further transformations to form more diversified four-membered compounds. Asymmetric synthesis of di-, tri-, and tetrasubstituted bioactive molecules has also been achieved. Systematic mechanistic studies and theoretical calculations have revealed the origin of the regioselectivity, the key hydrogenation transition state models, and the sequence of the double and triple hydrogenation processes. The work provides a new choice for the catalytic asymmetric synthesis of cyclobutanes and related structures and demonstrates the robustness of asymmetric transfer hydrogenation in the accurate selectivity control of highly functionalized substrates.Vir: Journal of the American Chemical Society [Elektronski vir]. - ISSN 1520-5126 (Vol. 146, iss. 7, 2024, str. 4942-4957)Vrsta gradiva - e-članek ; neleposlovje za odrasleLeto - 2024Jezik - angleškiCOBISS.SI-ID - 186768899
Avtor
Lan, Shouang |
Huang, Huangjiang |
Liu, Wenjun |
Xu, Chao |
Lei, Xiang |
Dong, Wennan |
Liu, Jinggong |
Yang, Shuang |
Cotman, Andrej Emanuel |
Zhang, Qi, kemičarka |
Fang, Xinqiang
Teme
Kemijske reakcije |
catalysts |
chemical reactions |
hydrogenation |
redox reactions |
katalizatorji |
kemijske reakcije |
hidrogenacija |
redoks reakcije
Vnos na polico
Trajna povezava
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Baze podatkov, v katerih je revija indeksirana
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Povezave do osebnih bibliografij avtorjev | Povezave do podatkov o raziskovalcih v sistemu SICRIS |
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Lan, Shouang | |
Huang, Huangjiang | |
Liu, Wenjun | |
Xu, Chao | |
Lei, Xiang | |
Dong, Wennan | |
Liu, Jinggong | |
Yang, Shuang | |
Cotman, Andrej Emanuel | 37459 |
Zhang, Qi, kemičarka | |
Fang, Xinqiang |
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