Organocatalyzed Enantioselective Direct Mannich Reaction of α-Styrylacetates
| Autor: | Ariel J. Larson, Manisha Bihani, Saroj Rout, Jie Guang, Hadi D. Arman, John C.-G. Zhao |
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| Rok vydání: | 2016 |
| Předmět: |
Molecular Structure
010405 organic chemistry Cinchona Alkaloids Organic Chemistry Enantioselective synthesis Esters Stereoisomerism Acetates 010402 general chemistry Highly selective 01 natural sciences Biochemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Organic chemistry Molecule Stereoselectivity Physical and Theoretical Chemistry Furans Mannich reaction Tetrahydrofuran |
| Zdroj: | Organic Letters. 18:2648-2651 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | An organocatalyzed direct Mannich reaction of unactivated α-styrylacetates was realized for the first time. By using a quinidine-derived C6'-urea catalyst, the direct Mannich reaction of α-styrylacetates and N-tosylimines gave the desired β-amino esters in high yields, diastereoselectivities, and ee values. The reaction provides a highly stereoselective (up to 96:4 dr and 97% ee) and the most straightforward synthesis of functionalized N-tosylated β-amino esters. The products can be used as precursors for the highly selective synthesis of tetrahydrofuran derivatives. |
| Databáze: | OpenAIRE |
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