Premium
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
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom