Remote Enantioselective ε‐Alkylation of Copper Ethynylallenylidenes: Precise Control of Central and Axial Chirality

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 17, 2024

Chiral tetrasubstituted allenes have emerged as important architectures for engineering biologically active compounds. The construction of unique allene scaffolds with precise control continuous central and axial chirality remains yet to be developed. Here, we report a remote enantioselective ϵ-alkylation yne-propargylic acetates enals enabled by NHC copper cooperative catalysis, leading series excellent enantioselectivities (up >99 % ee) diastereoselectivities >95 : 5 dr). This method features high regioselectivity simultaneous chirality. Mechanistic studies suggest activation mode synergistic distal created from the ethynylallenylidenes.

Language: Английский

Remote Enantioselective ε‐Alkylation of Copper Ethynylallenylidenes: Precise Control of Central and Axial Chirality

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 17, 2024

Abstract Chiral tetrasubstituted allenes have emerged as important architectures for engineering biologically active compounds. The construction of unique allene scaffolds with precise control continuous central and axial chirality remains yet to be developed. Here, we report a remote enantioselective ϵ‐alkylation yne‐propargylic acetates enals enabled by NHC copper cooperative catalysis, leading series excellent enantioselectivities (up >99 % ee) diastereoselectivities >95 : 5 dr). This method features high regioselectivity simultaneous chirality. Mechanistic studies suggest activation mode synergistic distal created from the ethynylallenylidenes.

Language: Английский