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Properties and Reactivity of Conformationally Constrained Bicyclic Diarylprolinol Silyl Ethers as Organocatalysts
Author(s) -
Lombardo Marco,
Cerisoli Lucia,
Mai Elisabetta,
Montroni Elisa,
Quintavalla Arianna,
Trombini Claudio
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402732
Subject(s) - chemistry , reactivity (psychology) , iminium , bicyclic molecule , silylation , enamine , silyl ether , organocatalysis , ether , catalysis , organic chemistry , stereochemistry , medicinal chemistry , enantioselective synthesis , alternative medicine , pathology , medicine
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.