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A New Family of Conformationally Constrained Bicyclic Diarylprolinol Silyl Ethers as Organocatalysts
Author(s) -
Lombardo Marco,
Montroni Elisa,
Quintavalla Arianna,
Trombini Claudio
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200922
Subject(s) - bicyclic molecule , chemistry , silyl ether , pyrrolidine , silylation , ether , catalysis , stereochemistry , organocatalysis , hydrolysis , ring (chemistry) , organic chemistry , enantioselective synthesis
Simple chemical manipulations of trans ‐4‐ L ‐hydroxy proline allow the access to a new family of bicyclic silyl ether organocatalysts that display some remarkable features. Apart from being extremely stable to hydrolytic conditions and possessing excellent catalytic performances, the rigidity of the bicyclic structure imposes a synclinal endo disposition of the bulky substituents with respect to the pyrrolidine ring, opposed to the more stable synclinal exo conformations of Jørgensen–Hayashi catalysts.