An unprecedented N-substituent of the amide was found to be crucial for the successful annulation to establish 2-azabicyclo[3.3.1]nonane and other ring skeletons in good yield. The novel catalytic aza-Wacker annulation methodology was further illustrated in the concise syntheses and the absolute configuration determinations of melinonine-E and strychnoxanthine.
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Pd/Cu-Cocatalyzed Enantio- and Diastereodivergent Wacker-Type Dicarbofunctionalization of Unactivated Alkenes.
J Am Chem Soc
September 2024
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
The Wacker and Wacker-type reactions are some of the most fundamental and powerful transformations in organic chemistry for their ability to efficiently produce valuable chemicals. Remarkable progress has been achieved in asymmetric oxy/aza-Wacker-type reactions; however, asymmetric Wacker-type dicarbofunctionalization remains underdeveloped, especially for the concurrent construction of two stereocenters. Herein, we report a Pd/Cu-cocatalyzed enantio- and diastereodivergent Wacker-type dicarbofunctionalization of alkene-tethered aryl triflates with imino esters.
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ACS Catal
June 2024
Institut für Organische Chemie, Universität Regensburg, Universitätstrasse 31, 93053 Regensburg, Germany.
Herein, the intermolecular, photoaerobic aza-Wacker coupling of azoles with alkenes by means of dual and ternary selenium-π-acid multicatalysis is presented. The title method permits an expedited avenue toward a broad scope of -allylated azoles and representative azinones under mild conditions with broad functional group tolerance, as is showcased in more than 60 examples including late-stage drug derivatizations. From a regiochemical perspective, the protocol is complementary to cognate photoredox catalytic olefin aminations, as they typically proceed through either allylic hydrogen atom abstraction or single electron oxidation of the alkene substrate.
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ChemSusChem
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Universität Göttingen, Institut für Anorganische Chemie, Tammannstrasse 4, 37077, Göttingen, Germany.
Article Synopsis
- A new light-driven catalytic process is introduced for creating 3-pyrrolines using a combination of disulfide assistance and selenium catalysts, achieving yields up to 95%.
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ACS Catal
December 2023
Institut Für Organische Chemie, Universität Regensburg, Universitätstrasse 31, 93053 Regensburg, Germany.
An adaptable, sulfur-accelerated photoaerobic selenium-π-acid ternary catalyst system for the enantioselective allylic redox functionalization of simple, nondirecting alkenes is reported. In contrast to related photoredox catalytic methods, which largely depend on olefinic substrates with heteroatomic directing groups to unfold high degrees of stereoinduction, the current protocol relies on chiral, spirocyclic selenium-π-acids that covalently bind to the alkene moiety. The performance of this ternary catalytic method is demonstrated in the asymmetric, photoaerobic lactonization and cycloamination of enoic acids and unsaturated sulfonamides, respectively, leading to an averaged enantiomeric ratio (er) of 92:8.
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Org Biomol Chem
July 2023
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Academician Kukhar str., 5, Kyiv 02660, Ukraine.
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