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EnglishBicyclic silyl ether derivatives 1, which are derived from simple chemical manipulations of trans-4-L-hydroxyproline, were recently proposed, by us, as conformationally constrained analogues of Jørgensen–Hayashi’s catalysts 2. Despite the structural similarities, 1 displays remarkable performance in iminium chemistry with respect to 2, but much lower reactivity in enamine chemistry. The peculiar structural features of 1 confer a pattern of reactivity between Jørgensen–Hayashi’s catalysts and MacMillan’s imidazolidinones.
| Titolo: | Properties and Reactivity of Conformationally Constrained Bicyclic Diarylprolinol Silyl Ethers as Organocatalysts | |
| Autore/i: | LOMBARDO, MARCO; CERISOLI, LUCIA; MANONI, ELISABETTA; MONTRONI, ELISA; QUINTAVALLA, ARIANNA; TROMBINI, CLAUDIO | |
| Autore/i Unibo: | ||
| Anno: | 2014 | |
| Rivista: | ||
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/ejoc.201402732 | |
| Abstract: | Bicyclic silyl ether derivatives 1, which are derived from simple chemical manipulations of trans-4-L-hydroxyproline, were recently proposed, by us, as conformationally constrained analogues of Jørgensen–Hayashi’s catalysts 2. Despite the structural similarities, 1 displays remarkable performance in iminium chemistry with respect to 2, but much lower reactivity in enamine chemistry. The peculiar structural features of 1 confer a pattern of reactivity between Jørgensen–Hayashi’s catalysts and MacMillan’s imidazolidinones. | |
| Data prodotto definitivo in UGOV: | 2014-11-11 15:01:09 | |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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http://hdl.handle.net/11585/342915
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