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