A Recyclable Chiral 2‐(Triphenylmethyl)pyrrolidine Organocatalyst Anchored to [60]Fullerene

Hybridization of a chiral 3‐hydroxy‐2‐trityl‐pyrrolidine deriving from (R)‐pyrrolidinol with [60]fullerene via click chemistry provides a highly efficient supported enantioselective organocatalyst, which was successfully exploited in a Michael addition of malonates to cinnamaldehydes, via iminium io...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-06, Vol.361 (12), p.2936-2944
Main Authors: Rosso, Cristian, Emma, Marco G., Martinelli, Ada, Lombardo, Marco, Quintavalla, Arianna, Trombini, Claudio, Syrgiannis, Zois, Prato, Maurizio
Format: Article
Language:English
Subjects:
Catalyst recycling
Chemical synthesis
Enantiomers
Enantioselective organocatalysis
Fullerene
Fullerenes
Michael addition
Organic chemistry
Supported trityl-pyrrolidine
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Summary:Hybridization of a chiral 3‐hydroxy‐2‐trityl‐pyrrolidine deriving from (R)‐pyrrolidinol with [60]fullerene via click chemistry provides a highly efficient supported enantioselective organocatalyst, which was successfully exploited in a Michael addition of malonates to cinnamaldehydes, via iminium ion activation. The supported organocatalyst was recycled up to six times, with only a moderate decrease in terms of activity and with no loss in enantioselectivity.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900009