Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans
Abstract
:1. Introduction
2. Results and Discussion
5a | CH3COCH2COOEt | 5e | EtCOOCH2COPh |
5b | CH3COCH2COCH3 | 5f | PhCH2COOCH2COCH3 |
5c | NCCH2CSNH2 | 5g | PhCOCH2CN |
5d | | 5h | |
Compound a | X | R1 | R2 | Yield (%) |
---|---|---|---|---|
6a | O | CH3 | COOEt | 72 |
6b | O | CH3 | COCH3 | 60 |
6c | S | NH2 | CN | 92 |
6d * | O | | 90 | |
6e | O | Ph | COOEt | 87 |
6f | O | CH3 | COOCH2Ph | 65 |
6g | O | Ph | CN | 83 |
6h * | O | | 78 |
Entry | Specific rotation [α]D 25 °C, c = 1, DMF |
---|---|
6a | +318.20 |
6e | +198.81 |
6h | +198.20 |
4 | +247.02 |
13 | +272.0 |
3. Experimental
3.1. General
3.2. General Experimental Procedure for the Synthesis of Pyrans 6a–h and Compound 7
3.3. Experimental Procedure for the Synthesis of 4
3.4. Experimental Procedure for the Synthesis of 13
4. Conclusions
Acknowledgments
References and Notes
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- CCDC 850090-850094 and 851560 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via “http://www.ccdc.cam.ac.uk/data_request/cif”.
- Sample Availability:Samples of the compounds 6a–h, 4 and 13 are available from the authors.
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Elnagdi, N.M.H.; Al-Hokbany, N.S. Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans. Molecules 2012, 17, 4300-4312. https://doi.org/10.3390/molecules17044300
Elnagdi NMH, Al-Hokbany NS. Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans. Molecules. 2012; 17(4):4300-4312. https://doi.org/10.3390/molecules17044300
Chicago/Turabian StyleElnagdi, Noha M. Hilmy, and Noura Saad Al-Hokbany. 2012. "Organocatalysis in Synthesis: L-Proline as an Enantioselective Catalyst in the Synthesis of Pyrans and Thiopyrans" Molecules 17, no. 4: 4300-4312. https://doi.org/10.3390/molecules17044300