ol500355z_si_001.pdf (3.41 MB)
Development of (Trimethylsilyl)ethyl Ester Protected Enolates and Applications in Palladium-Catalyzed Enantioselective Allylic Alkylation: Intermolecular Cross-Coupling of Functionalized Electrophiles
journal contribution
posted on 2015-12-17, 04:20 authored by Corey
M. Reeves, Douglas C. Behenna, Brian M. StoltzThe development of (trimethylsilyl)ethyl
ester protected enolates
is reported. The application of this class of compounds in palladium-catalyzed
asymmetric allylic alkylation is explored, yielding a variety of α-quaternary
six- and seven-membered ketones and lactams. Independent coupling
partner synthesis engenders enhanced allyl substrate scope relative
to traditional β-ketoester substrates; highly functionalized
α-quaternary ketones generated by the union of (trimethylsilyl)ethyl
β-ketoesters and sensitive allylic alkylation coupling partners
serve to demonstrate the utility of this method for complex fragment
coupling.
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allylic alkylationEnantioselectivefunctionalizedAllyliccompoundApplicationEsterAlkylationenolateIndependentvarietyunionapplicationTrimethylsilylesterutilitymethodsynthesisallyl substrate scopeketoesterfragmentProtectedtrimethylsilyllactamketonequaternaryFunctionalized ElectrophilesThe developmentIntermolecularEnolate
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