Peptide-Catalyzed Desymmetrization of an Achiral Ferrocenyl Compound To Induce Planar Chirality

Selective monohydrogenation of an achiral ferrocenebis(enal) was achieved with a resin‐supported peptide catalyst to afford an enantioenriched planar‐chiral product. It was also demonstrated that the reaction was followed by a kinetic resolution through cyclization of the product. Planar chirality w...

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Veröffentlicht in:European journal of organic chemistry 2015-06, Vol.2015 (18), p.3894-3898
Hauptverfasser: Akagawa, Kengo, Akiyama, Midori, Kudo, Kazuaki
Format: Artikel
Sprache:eng
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Zusammenfassung:Selective monohydrogenation of an achiral ferrocenebis(enal) was achieved with a resin‐supported peptide catalyst to afford an enantioenriched planar‐chiral product. It was also demonstrated that the reaction was followed by a kinetic resolution through cyclization of the product. Planar chirality was induced on an achiral ferrocenyl compound by peptide‐catalyzed desymmetrization. Although such an asymmetric reaction could not be realized with a low‐molecular‐weight catalyst, a resin‐supported peptide with a turn structure afforded products in a highly enantioselective manner.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500428