Catalytic Reductive Pinacol-Type Rearrangement of Unactivated 1,2-Diols through a Concerted, Stereoinvertive Mechanism
| Autor: | Erhan Ozkal, Walter Thiel, Nikolaos Drosos, Bastien Cacherat, Gui-Juan Cheng, Bill Morandi |
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| Rok vydání: | 2017 |
| Předmět: |
inorganic chemicals
Silanes 010405 organic chemistry Pinacol Concerted reaction organic chemicals Diol General Medicine General Chemistry 010402 general chemistry Pinacol rearrangement 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Organic chemistry heterocyclic compounds Rearrangement reaction Deoxygenation |
| Zdroj: | Angewandte Chemie International Edition. 56:13377-13381 |
| ISSN: | 1433-7851 |
| DOI: | 10.1002/anie.201704936 |
| Popis: | A catalytic pinacol-type reductive rearrangement reaction of internal 1,2-diols is reported herein. Several scaffolds not usually amenable to pinacol-type reactions, such as aliphatic secondary-secondary diols, undergo the transformation well without the need for prefunctionalization. The reaction uses a simple boron catalyst and two silanes and proceeds through a concerted, stereoinvertive mechanism that enables the preparation of highly enantiomerically enriched products. Computational studies have been used to rationalize the preference for migration over direct deoxygenation. |
| Databáze: | OpenAIRE |
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