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.
Properties and Reactivity of Conformationally Constrained Bicyclic Diarylprolinol Silyl Ethers as Organocatalysts / Marco Lombardo; Lucia Cerisoli; Elisabetta Manoni; Elisa Montroni; Arianna Quintavalla; Claudio Trombini. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2014:(2014), pp. 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.
