Proline Sulfonamide-Catalyzed, Domino Process for Asymmetric Synthesis of Amino- and Hydroxy-Substituted Bicyclo[2.2.2]octanes
| Autor: | Rajinikanth Lingampally, Mohamed F. El-Mansy, Jun Yong Kang, Rich G. Carter |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
chemistry.chemical_classification
Bicyclic molecule 010405 organic chemistry Stereochemistry Organic Chemistry Enantioselective synthesis 010402 general chemistry 01 natural sciences 0104 chemical sciences Sulfonamide Catalysis chemistry Organocatalysis Stereoselectivity Domino process Proline Physical and Theoretical Chemistry |
| Zdroj: | European Journal of Organic Chemistry. 2016:150-157 |
| ISSN: | 1434-193X |
| DOI: | 10.1002/ejoc.201501302 |
| Popis: | A generalized method for accessing highly functionalized amino-substituted bicyclo[2.2.2]octanes via p-dodecylphenylsulfonamide catalyst in a good enantio- and diastereoselective fashion has been developed. A discussion of the mechanistic underpinnings of this transformation is presented. Finally, an unexpected discovery enabling the extension of this protocol to the synthesis of OH-substituted bicyclo[2.2.2]octanes with encouraging levels of stereoselectivity is discussed. |
| Databáze: | OpenAIRE |
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