Enantioselective, Organocatalytic Reduction of Ketones using Bifunctional Thiourea-Amine Catalysts
| Autor: | Anyu He, John R. Falck, De Run Li |
|---|---|
| Rok vydání: | 2010 |
| Předmět: |
Chemistry
Organic Chemistry Thiourea Enantioselective synthesis Stereoisomerism Ketones Borane Biochemistry Asymmetric induction Catalysis Article Substrate Specificity chemistry.chemical_compound Cross-Linking Reagents Nucleophile Organic chemistry Amine gas treating Amines Physical and Theoretical Chemistry Bifunctional Oxidation-Reduction Catecholborane |
| Zdroj: | Organic Letters. 12:1756-1759 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol100365c |
| Popis: | Prochiral ketones are reduced to enantioenriched, secondary alcohols using catecholborane and a family of air-stable, bifunctional thiourea-amine organocatalysts. Asymmetric induction is proposed to arise from the in situ complexation between the borane and chiral thiourea-amine organocatalyst resulting in a stereochemically biased boronate-amine complex. The hydride in the complex is endowed with enhanced nucleophilicity while the thiourea concomitantly embraces and activates the carbonyl. |
| Databáze: | OpenAIRE |
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