Proposed Mechanism for the Enantioselective Alkynylation of an Aryl Trifluoromethyl Ketone, the Key Step in the Synthesis of Efavirenz
| Autor: | Aleksander Warm, Gareth J. Griffiths |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Efavirenz
010405 organic chemistry Aryl Organic Chemistry Enantioselective synthesis Alcohol 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Alkynylation Mechanism (philosophy) Trifluoromethyl ketone Organic chemistry Physical and Theoretical Chemistry |
| Zdroj: | Organic Process Research & Development. 20:803-813 |
| ISSN: | 1520-586X 1083-6160 |
| DOI: | 10.1021/acs.oprd.6b00058 |
| Popis: | The rationalization of observations made during optimization of the zinc-mediated enantioselective addition of cyclopropylacetylene (2) to ketoaniline 8 in the presence of (1R,2S)-1-phenyl-2-(pyrrolidin-1-yl)propan-1-ol (3) to afford amino alcohol 11 has enabled us to propose a mechanism for this transformation. The proposed mechanism has been used as the basis for the development of a spreadsheet-based mass-balance simulation, which has proved useful in predicting the effects of stoichiometry changes and in process troubleshooting. |
| Databáze: | OpenAIRE |
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