Hydrogen borrowing catalysis using 1° and 2° alcohols: investigation and scope leading to α and β branched products
| Autor: | Neil G. Stevenson, Choon Boon Cheong, Dimitri F. J. Caputo, Kirsten E. Christensen, Timothy J. Donohoe, James R. Frost, Wasim M. Akhtar |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Hydrogen
Scope (project management) 010405 organic chemistry Aryl Organic Chemistry chemistry.chemical_element Alkylation 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Intramolecular force Drug Discovery |
| Popis: | The alkylation of a variety of ketones using 1° or 2° alcohols under hydrogen borrowing catalysis is described. Initial research focused on the α-alkylation of cyclopropyl ketones with higher 1° alcohols (i.e. larger than MeOH), leading to the formation of α-branched products. Our search for additional substrates with which to explore this chemistry led us to discover that di-ortho-substituted aryl ketones were also privileged scaffolds, with Ph∗ (C6Me5) ketones being the optimal choice. Further investigations revealed that this motif was crucial for alkylation with 2° alcohols forming β-branched products, which also provided an opportunity to study diastereoselective and intramolecular hydrogen borrowing processes. |
| Databáze: | OpenAIRE |
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