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Asymmetric Catalysis: Resin-Bound Hydroxyprolylthreonine Derivatives in Enamine-Mediated Reactions

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  • This work was supported by the National Science Foundation (NSF; CHE-0614756) and the National Institute for General Medical Sciences (GM076151). NMR spectrometers used in this work were funded in part by the NSF (CHE-0443516 and CHE-9808183). RDC thanks the American Chemical Society's Division of Medicinal Chemistry for Predoctoral Fellowship support (sponsored by Sanofi-Aventis), the Howard Hughes Medical Institute for their Med into Grad Fellowship, and UC Davis for their R. Bryan Miller Graduate Fellowship.

Abstract

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Zwei immobilisierte Hydroxyprolylthreonin-Katalysatoren mit zwei tert-Butoxy-Schutzgruppen (siehe Struktur, die Kugel repräsentiert die TentaGel-Festphase) vermitteln asymmetrische Enamin-/Michael-Tandemreaktionen mit hoher Enantioselektivität und vollständiger Diastereoselektivität. Die gewünschte absolute Konfiguration bestimmt die Wahl des Katalysators.

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