Journal ArticleDOI
Regio- and Stereoselective Modification of Chiral α-Amino Ketones by Pd-Catalyzed Allylic Alkylation.
TLDR
This approach can be used for the synthesis of highly substituted piperidine derivatives and can be reduced stereoselectively, and up to five consecutive stereogenic centers can be obtained.Abstract:
Chiral α-amino ketones are excellent nucleophiles for stereoselective palladium-catalyzed allylic alkylations. Both chiral as well as achiral allylic substrates can be applied, while the stereochemical outcome of the reaction is controlled by the chiral ketone enolate. The substituted amino ketones formed can be reduced stereoselectively, and up to five consecutive stereogenic centers can be obtained. This approach can be used for the synthesis of highly substituted piperidine derivatives.read more
Citations
More filters
Journal ArticleDOI
Stereoselective and Site-Specific Allylic Alkylation of Amino Acids and Small Peptides via a Pd/Cu Dual Catalysis
TL;DR: A direct and highly stereoselective synthesis of small peptides with enantiopure α-alkyl or α,α-dialkyl α-amino acids residues incorporated at specific sites was accomplished using this dual catalyst system.
Journal ArticleDOI
Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles
Kaluvu Balaraman,Christian Wolf +1 more
TL;DR: A new C-F bond functionalization path that provides unprecedented possibilities for the stereoselective generation of a chiral quaternary carbon center in the alkaloid scaffold is introduced.
Journal ArticleDOI
Iridium‐Catalyzed Diastereoselective and Enantioselective Allylic Substitutions with Acyclic α‐Alkoxy Ketones
TL;DR: These reactions occur between allyl methyl carbonates and unstabilized copper(I) enolates generated in situ from acyclic α-alkoxy ketones and can be readily converted into enantioenriched tertiary alcohols and tetrahydrofuran derivatives without erosion of enantiomeric purity.
Journal ArticleDOI
Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.
Xingyu Jiang,John F. Hartwig +1 more
TL;DR: In this paper, the iridium-catalyzed enantioselective allylation reactions of silyl ketene acetals, the silicon enolates of esters, to form products containing a quaternary carbon atom at the nucleophile moiety and a tertiary carbon atom in the electrophile moiety were reported.
Journal ArticleDOI
Planar-Chiral Cyclopentadienyl-Ruthenium-Catalyzed Regio- and Enantioselective Asymmetric Allylic Alkylation of Silyl Enolates under Unusually Mild Conditions
TL;DR: In this article, the asymmetric allylic alkylation of allylic chlorides with silyl enolates as a carbon nucleophile using a planar-chiral cyclopentadienyl-ruthenium (Cp′Ru) catalyst was reported.
References
More filters
Journal ArticleDOI
Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.
TL;DR: Alkylations with Phenols, Nitrogen Nucleophiles in AAA Total Synthesis, and Considerations for Enantioselective Allylic Alkylation are presented.
Journal ArticleDOI
Metal-catalyzed enantioselective allylation in asymmetric synthesis.
TL;DR: Metal-catalyzed enantioselective allylation, which involves the substitution of allylic metal intermediates with a diverse range of different nucleophiles or S(N)2'-type allylic substitution, leads to the formation of C-H, -C, -O, -N, -S, and other bonds with very high levels of asymmetric induction.
Journal ArticleDOI
Allylic 1,3-strain as a controlling factor in stereoselective transformations
TL;DR: In this article, the authors present a model for controlling dyadic add-ion reactions to double-branched double-bond reactions, including the following: 1.3-Strain Control of Dlastereoselective Intermolecular Addhion Reactions InvoMng Heteroallyl Systems 10.5.
Journal ArticleDOI
Asymmetric allylic alkylation, an enabling methodology.
TL;DR: The diversity of mechanisms for enantiodiscrimination and of bond types that can be formed make Pd-catalyzed asymmetric allylic alkylation a powerful key step for simplification of synthetic strategy to complex molecular targets.
Journal ArticleDOI
Metallkatalysierte enantioselektive Allylierungen in der asymmetrischen Synthese
TL;DR: In this article, metallkatalysierte enantioselektive Allylierungen, die unter Substitution von Allylmetall-Zwischenstufen mit zahlreichen Nucleophilen oder als allylische SN2′-Substitution verlaufen, werden in Gegenwart ausgewahlter Kombinationen aus Metallen and chiralen Liganden C-H-, C-C-, C-, C O-, C N-, C S