Enantioselective Propargylic Alkylation Research Articles

Cooperative Ni/Cu‐Catalyzed Asymmetric Propargylic Alkylation of Aldimine Esters

AbstractA novel Ni/Cu dual catalysis gives rise to fundamentally new cooperative reactivity and enables the regio‐ and enantioselective propargylic alkylation reaction. A diverse set of α‐quaternary propargylated amino ester derivatives were synthesized in good yields with excellent enantioselectivity (up to 99 % ee). This work highlights the power of cooperative catalysis, which can be expected to have broad implications in homogeneous catalysis beyond the highly valuable synthetic intermediates.

Cooperative catalysis: enantioselective propargylic alkylation of propargylic alcohols with enecarbamates using ruthenium/phosphoramide hybrid catalysts.

The diastereo- and enantioselective propargylic alkylation of propargylic alcohols with E-enecarbamates in the presence of a catalytic amount of thiolate-bridged diruthenium complexes bearing an optically active phosphoramide moiety gives the corresponding propargylic alkylated products (up to 97 % ee).

Cooperative Catalysis: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Enecarbamates Using Ruthenium/Phosphoramide Hybrid Catalysts

AbstractThe diastereo‐ and enantioselective propargylic alkylation of propargylic alcohols with E‐enecarbamates in the presence of a catalytic amount of thiolate‐bridged diruthenium complexes bearing an optically active phosphoramide moiety gives the corresponding propargylic alkylated products (up to 97 % ee).

ChemInform Abstract: Cooperative Catalytic Reactions Using Distinct Transition‐Metal Catalysts: Ruthenium‐ and Copper‐Catalyzed Enantioselective Propargylic Alkylation.

AbstractA Ru—Cu co‐catalyzed reaction of β‐ketoesters with propargylic alcohols is described, which provides the products (III) in high yields and enantioselectivities (up to 93% e.e.).

Ruthenium- and Copper-Catalyzed Enantioselective Propargylic Alkylation of Propargylic Alcohols with β-Keto Phosphonates

The enantioselective propargylic alkylation of propargylic alcohols with β-keto phosphonates in the presence of a thiolate-bridged diruthenium complex and a copper complex as cocatalysts gives the ...

ChemInform Abstract: Cooperative Catalytic Reactions Using Lewis Acids and Organocatalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols Bearing an Internal Alkyne with Aldehydes.

AbstractAn optically active secondary amine is used as co‐catalyst in the title reaction affording the corresponding propargylic alkylated products in high yields as a mixture of two diastereoisomers with high enantioselectivity.

ChemInform Abstract: Cooperative Catalytic Reactions Using Organocatalysts and Transition Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Esters with Aldehydes.

AbstractIn the presence of CuOTf, BINAP, and the prolinol (PRO) propargylic esters are found to undergo highly enantioselective reaction with aldehydes to afford alcohols like (III), (IV), (VI), and (VII).

Cooperative Catalytic Reactions Using Lewis Acids and Organocatalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols Bearing an Internal Alkyne with Aldehydes (Eur. J. Org. Chem. 12/2011)

AbstractThe cover picture shows that both wings are necessary for a butterfly to fly. Likewise, both a Lewis acid and an organocatalyst contribute cooperatively to the catalytic enantioselective propargylic alkylation of proparglylic alcohols bearing an internal alkyne moiety with aldehydes. Details are discussed in the article by Y. Nishibayashi et al. on p. 2239 ff.

Graphical Abstract: Eur. J. Org. Chem. 12/2011

AbstractThe cover picture shows that both wings are necessary for a butterfly to fly. Likewise, both a Lewis acid and an organocatalyst contribute cooperatively to the catalytic enantioselective propargylic alkylation of proparglylic alcohols bearing an internal alkyne moiety with aldehydes. Details are discussed in the article by Y. Nishibayashi et al. on p. 2239 ff.

Cooperative Catalytic Reactions Using Lewis Acids and Organocatalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols Bearing an Internal Alkyne with Aldehydes

AbstractThe enantioselective propargylic alkylation of propargylic alcohols bearing an internal alkyne moiety with aldehydes in the presence of a metal salt as the Lewis acid and an optically active secondary amine as the co‐catalyst has been found to give the corresponding propargylic alkylated products in high yields as a mixture of two diastereoisomers with high enantioselectivity.

ChemInform Abstract: Cooperative Catalytic Reactions Using Organocatalysts and Transition‐Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Aldehydes.

AbstractA thiolate‐bridged diruthenium complex and a prolinol‐derived secondary amine are used as catalysts.

Cooperative Catalytic Reactions Using Organocatalysts and Transition Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Esters with Aldehydes

The enantioselective propargylic alkylation of propargylic esters with aldehydes in the presence of a copper complex and an optically active secondary amine as cocatalysts has been found to give the corresponding propargylic alkylated products in good yields as a mixture of two diastereoisomers with a high enantioselectivity.

Cooperative Catalytic Reactions Using Organocatalysts and Transition‐Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Aldehydes

Working together: The title reaction proceeds in the presence of a thiolate-bridged diruthenium complex (2) and a secondary amine (1) to give the corresponding propargylic alkylated products in excellent yields as a mixture of two diastereoisomers, each with high enantioselectivity. The two catalysts activate propargylic alcohols and aldehydes, respectively, and cooperatively promote the enantioselective reaction.

Cover Picture: Cooperative Catalytic Reactions Using Organocatalysts and Transition-Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Aldehydes (Angew. Chem. Int. Ed. 40/2010)

Cover Picture: Cooperative Catalytic Reactions Using Organocatalysts and Transition-Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Aldehydes (Angew. Chem. Int. Ed. 40/2010)

Cooperative Catalytic Reactions Using Organocatalysts and Transition‐Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Aldehydes

Cooperative Catalytic Reactions Using Organocatalysts and Transition‐Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Aldehydes

Synthesis of Diruthenium Complexes Containing Chiral Thiolate-Bridged Ligands and Their Application to Catalytic Propargylic Alkylation of Propargylic Alcohols with Acetone

Novel diruthenium complexes containing chiral thiolate-bridged ligands are synthesized and characterized crystallographically. The chiral diruthenium complexes promote enantioselective propargylic alkylation of propargylic alcohols with acetone to give the corresponding propargylic alkylated products in good yields with moderate enantioselectivities (up to 35% ee).