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A Recyclable Chiral 2‐(Triphenylmethyl)pyrrolidine Organocatalyst Anchored to [60]Fullerene
Author(s) -
Rosso Cristian,
Emma Marco G.,
Martinelli Ada,
Lombardo Marco,
Quintavalla Arianna,
Trombini Claudio,
Syrgiannis Zois,
Prato Maurizio
Publication year - 2019
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.201900009
Subject(s) - chemistry , pyrrolidine , enantioselective synthesis , iminium , organocatalysis , fullerene , combinatorial chemistry , organic chemistry , fullerene chemistry , catalysis
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.