Control of the Organocatalytic Enantioselective α-Alkylation of Vinylogous Carbonyl Enolates for the Synthesis of Tetrahydropyran Derivatives and Beyond
| Autor: | Su-Ying Chien, Yung-Ju Wang, Pavan Sudheer Akula, Gene-Hsiang Lee, Bor-Cherng Hong |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Ketone 010405 organic chemistry Chemistry Organic Chemistry Enantioselective synthesis Tetrahydropyran Alkylation 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences chemistry.chemical_compound Organic chemistry Hemiacetal Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 23:4688-4693 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.1c01426 |
| Popis: | The organocatalytic α-alkylation of vinylogous carbonyl compounds to hydroxynitroolefins for the synthesis of hemiacetals was realized with excellent enantioselectivities and in high yields. High diastereoselectivity (up to >20:1) has been accomplished with the addition of Et3N. The α- and γ-alkylation of vinylogous ketone against nitroolefins displayed high but opposite facial selectivities. Transformation of the hemiacetal products to other polycyclic compounds, including the euroticin B analog, has been demonstrated. |
| Databáze: | OpenAIRE |
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