Mild and Efficient Desymmetrization of Diynes via Hydroamination: Application to the Synthesis of (±)-Monomorine I
| Autor: | Vijaya Bhaskara Reddy Iska, Olaf Wiest, Vincenzo Verdolino, Paul Helquist |
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| Rok vydání: | 2010 |
| Předmět: |
Models
Molecular Magnetic Resonance Spectroscopy Silver Molecular Structure Organic Chemistry Indolizines Stereoisomerism Chemical synthesis Desymmetrization Catalysis Transition state Diynes chemistry.chemical_compound chemistry Organic chemistry Pyrroles Amine gas treating Hydroamination Amination Monomorine I |
| Zdroj: | The Journal of Organic Chemistry. 75:1325-1328 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo902674j |
| Popis: | An efficient silver-catalyzed desymmetrization of amino diynes via hydroamination is reported. A variety of functionalized 1-pyrroline derivatives were synthesized in 73% to 88% isolated yields (98% by (1)H NMR in some cases). The usefulness of this mild hydroamination method was further shown by the desymmetrization of unprotected tert-hydroxy diynes. Structures of two transition states have been studied computationally. An application of this method was demonstrated by a short and efficient synthesis of (+/-)-monomorine I. |
| Databáze: | OpenAIRE |
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