2015
DOI: 10.3762/bjoc.11.83
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Multivalent polyglycerol supported imidazolidin-4-one organocatalysts for enantioselective Friedel–Crafts alkylations

Abstract: SummaryThe first immobilization of a MacMillan’s first generation organocatalyst onto dendritic support is described. A modified tyrosine-based imidazolidin-4-one was grafted to a soluble high-loading hyperbranched polyglycerol via a copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction and readily purified by dialysis. The efficiency of differently functionalized multivalent organocatalysts 4a–c was tested in the asymmetric Friedel–Crafts alkylation of N-methylpyrrole with α,β-unsaturated aldehydes. A … Show more

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Cited by 15 publications
(12 citation statements)
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“…Electron‐deficient aromatic enals 219 d,e provided greater selectivities and yields, approving the strong effect of the substituent. Defiantly, aliphatic enals 219 a,b were well‐reacted and the results have been not affected considerably …”
Section: Organocatalyzed Asymmetric Friedel‐crafts Reactions Usingmentioning
confidence: 94%
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“…Electron‐deficient aromatic enals 219 d,e provided greater selectivities and yields, approving the strong effect of the substituent. Defiantly, aliphatic enals 219 a,b were well‐reacted and the results have been not affected considerably …”
Section: Organocatalyzed Asymmetric Friedel‐crafts Reactions Usingmentioning
confidence: 94%
“…In 2015, the initial immobilization of a MacMillan's first generation organocatalyst onto dendritic support was demonstrated . An improved tyrosine‐based imidazolidin‐4‐one was attached to a soluble high‐loading hyperbranched polyglycerol through a Cu‐mediated alkyne‐azide cycloaddition (CuAAC) reaction and easily purified by dialysis.…”
Section: Organocatalyzed Asymmetric Friedel‐crafts Reactions Usingmentioning
confidence: 99%
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“…However, its practical use in reactions is still hindered due to the need for high catalyst loading and difficulties in recovering the catalyst from the reaction mixture. One obvious way to overcome these problems is to immobilizing or attaching the catalyst unit on a recyclable support , such as PEG [11], dendrimer [12,13], siliceous and polymer-coated mesocellular foam (MCF) [14], fluorous tag [15], poly(-methyl-hydrosiloxane) (PHMS) [16], ionic liquid [17][18][19][20].…”
Section: Inroductionmentioning
confidence: 99%