Hydrophosphination of Propargylic Alcohols and Amines with Phosphine Boranes
| Autor: | Michael Spinelli, Jiang-Ping Wu, Austin Gold, Anjan Saha, Chris H. Senanayake, Zhibin Li, Carl A. Busacca, Nizar Haddad, Elisa Farber, Bo Qu, Nicole Grět, Shengli Ma, Nelu Grinberg, Heewon Lee, Magnus C. Eriksson, Steve Han, Peter Wipf, Guijun Wang, Keith R. Fandrick |
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| Rok vydání: | 2013 |
| Předmět: |
Molecular Structure
Phosphines Propanols Chemistry Organic Chemistry Diastereomer Enantioselective synthesis Stereoisomerism Boranes Borane Biochemistry Catalysis Pyrophoricity chemistry.chemical_compound Alkynes Hydrophosphination Organic chemistry Fractional crystallization (chemistry) Amines Physical and Theoretical Chemistry Phosphine |
| Zdroj: | Organic Letters. 15:1132-1135 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | The first uncatalyzed hydrophosphinations of propargylic amines and alcohols with phosphine- borane complexes are described. The reactions proceed at ambient temperature or below without the use of protecting groups or the need to handle pyrophoric secondary phosphines, furnishing air-stable phosphineborane-amines and alcohols in good yields. Utilization of chiral propargylic substrates and unsymmetrical secondary phosphineboranes leads to diastereomeric P-chiral products that can be separated by fractional crystallization or chromatography. Initial applications of these new P-X species to asymmetric catalysis are detailed. |
| Databáze: | OpenAIRE |
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