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.
Marco Lombardo, Lucia Cerisoli, Elisabetta Manoni, Elisa Montroni, Arianna Quintavalla, Claudio Trombini (2014). Properties and Reactivity of Conformationally Constrained Bicyclic Diarylprolinol Silyl Ethers as Organocatalysts. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 5946-5953 [10.1002/ejoc.201402732].
Properties and Reactivity of Conformationally Constrained Bicyclic Diarylprolinol Silyl Ethers as Organocatalysts
LOMBARDO, MARCO;CERISOLI, LUCIA;MANONI, ELISABETTA;MONTRONI, ELISA;QUINTAVALLA, ARIANNA;TROMBINI, CLAUDIO
2014
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
