Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis
Abstract
:Introduction
Results and Discussion
Entry | Catalyst | Yield (%) [b] | erythro/threo [c] |
---|---|---|---|
1 | - | 0 | - |
2 | 1 | 45 | 70/30 |
3 | 2 | 63 | 80/20 |
4 | 3 | 12 | 70/30 |
5 | 4 | 30 | 70/30 |
6 | 5 | 16 | 60/40 |
7 | 6 | 25 | 70/30 |
8 | 6 | 0 | - |
Entry | Catalyst (mol%) | °C/h | Yield (%) [b] | erythro/threo [c] |
---|---|---|---|---|
1[a] | 1 (20) | 25°/48 | 82 | 70/30 |
2[a] | 1 (20) | 25°/72 | 18 | 70/30 |
3[a] | 1 (20) | 40°/24 | 7 | 70/30 |
4[a] | 2 (20) | 25°/48 | 74 | 70/30 |
5[a] | 2 (20) | 40°/48 | 34 | 78/22 |
Entry | Substrate | Yield (%)[b] with 1 | Yield (%)[b] with 2 | erythro/threo[c] with 1 | erythro/threo[c] with 2 |
---|---|---|---|---|---|
1 | p-CH3-C6H4CHO (8b) | 40 | 40 | 80/20 | 80/20 |
2 | p-CF3-C6H4 CHO (8c) | 58 | 50 | 70/30 | 70/30 |
3 | p-OCH3-C6H4 CHO (8d) | 25 | 4 | 80/20 | - |
4 | o-OCH3-C6H4 CHO (8e) | 15 | 0 | 70/30 | - |
5 | | 70 | 56 | 70/30 | 70/30 |
6 | C7H15 CHO (8g) | 30 | 40 | 70/30 | 70/30 |
7 | C10H21 CHO (8h) | 16 | 30 | 70/30 | 70/30 |
8 | CH3COCOOEt (8i) | 63 | 63 | 70/30 | 70/30 |
Experimental
General
General Procedure for the Organocatalytic Addition of TMSOF to Aldehydes
Conclusions
Acknowledgements
References
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Cafeo, G.; De Rosa, M.; Kohnke, F.H.; Soriente, A.; Talotta, C.; Valenti, L. Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis. Molecules 2009, 14, 2594-2601. https://doi.org/10.3390/molecules14072594
Cafeo G, De Rosa M, Kohnke FH, Soriente A, Talotta C, Valenti L. Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis. Molecules. 2009; 14(7):2594-2601. https://doi.org/10.3390/molecules14072594
Chicago/Turabian StyleCafeo, Grazia, Margherita De Rosa, Franz H. Kohnke, Annunziata Soriente, Carmen Talotta, and Luca Valenti. 2009. "Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis" Molecules 14, no. 7: 2594-2601. https://doi.org/10.3390/molecules14072594