Development of (Trimethylsilyl)ethyl Ester Protected Enolates and Applications in Palladium-Catalyzed Enantioselective Allylic Alkylation: Intermolecular Cross-Coupling of Functionalized Electrophiles Corey M. Reeves Douglas C. Behenna Brian M. Stoltz 10.1021/ol500355z.s001 https://acs.figshare.com/articles/journal_contribution/Development_of_Trimethylsilyl_ethyl_Ester_Protected_Enolates_and_Applications_in_Palladium_Catalyzed_Enantioselective_Allylic_Alkylation_Intermolecular_Cross_Coupling_of_Functionalized_Electrophiles/2039595 The 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. 2015-12-17 04:20:01 allylic alkylation Enantioselective functionalized Allylic compound Application Ester Alkylation enolate Independent variety union application Trimethylsilyl ester utility method synthesis allyl substrate scope ketoester fragment Protected trimethylsilyl lactam ketone quaternary Functionalized ElectrophilesThe development Intermolecular Enolate