Brønsted acid and Pd–PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes
| Autor: | Steven J. Malcolmson, Nathan J. Adamson, Sangjune Park |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Enantioselective synthesis General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences 3. Good health Stereocenter chemistry.chemical_compound chemistry Catalytic cycle Nucleophile Counterion Brønsted–Lowry acid–base theory Alkyl Malononitrile |
| Zdroj: | Chemical Science. 10:5176-5182 |
| ISSN: | 2041-6539 2041-6520 |
| DOI: | 10.1039/c9sc00633h |
| Popis: | We describe the development of Pd–PHOX-catalysed enantioselective couplings of internal dienes with malononitrile and other activated C-pronucleophiles. Reactions are dramatically accelerated by the addition of Et3N·HBArF4 as a Bronsted acid co-catalyst, enabling a suite of products bearing a variety of alkyl substituents at the stereogenic carbon to be prepared. A series of mechanism-oriented experiments reveal key aspects of the catalytic cycle and the importance of the non-coordinating BArF4 counterion in not only promoting reactions of internal dienes but also additions of previously unreactive nucleophiles towards terminal dienes. |
| Databáze: | OpenAIRE |
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