Enantioselective Dicarbofunctionalization of Unactivated Alkenes by Palladium-Catalyzed Tandem Heck/Suzuki Coupling Reaction
| Autor: | Yuanqi Wu, Yu Liu, Yanyan Qian, Bing Xu, Zhan-Ming Zhang, Junliang Zhang, Lujia Zhou, Lizuo Wu |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Molecular Structure 010405 organic chemistry Alkene Aryl Enantioselective synthesis chemistry.chemical_element General Chemistry General Medicine Alkenes 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Stereocenter chemistry.chemical_compound chemistry Suzuki reaction Alkyl Palladium |
| Zdroj: | Angewandte Chemie (International ed. in English). 58(41) |
| ISSN: | 1521-3773 |
| Popis: | A highly enantioselective dicarbofunctionalization of unactivated alkenes was implemented by a Pd-catalyzed asymmetric tandem Heck/Suzuki coupling reaction. This reaction represents the first example of a highly enantioselective intramolecular cyclization/cross-coupling of olefin-tethered aryl halides with alkyl-, alkenyl- or arylboronic acids, and provides rapid access to a number of chiral compounds, such as dihydrobenzofurans, indolines, chromanes, and indanes bearing a quaternary stereocenter, in good yields with excellent enantioselectivities. The practicality of this reaction was validated in the modification of biologically complex molecules such as peptides, piperitol, CB2 receptor agonists, etc. Moreover, the synthesis of two enantiomers can be easily realized by simple change in the order of the steps in the coupling sequence. |
| Databáze: | OpenAIRE |
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