Remote Copper-Catalyzed Atroposelective Synthesis of N–N Axially Chiral Compounds Bearing Minimally Different Alkyl Groups DOI

Zhaoliang Ge,

Cuiju Zhu,

Guang Xu

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 25, 2025

Herein, we report a copper-catalyzed remote asymmetric [4+1] annulation/aromatization between yne-allylic esters and N-aminoindoles, providing axially chiral N,N'-indolepyrroles that contain sterically comparable ortho substituents, such as methyl ethyl. This reaction proceeds smoothly under mild conditions, affording products with excellent regio- enantioselectivities while demonstrating broad functional group compatibility. The synthetic utility of this approach is further showcased through the late-stage modification biologically relevant scaffolds. Additionally, preliminary mechanistic investigations indicate nucleophilic substitution enantio-determining step.

Язык: Английский

Catalytic atroposelective synthesis of indolyl quinazolinones bearing N–N/C–C diaxes DOI

Ning‐Yi Wang,

Shuo Gao,

Zhiwei Shu

и другие.

Science China Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 9, 2025

Язык: Английский

Процитировано

6
Atroposelective [4+1] Annulation for the Synthesis of Isotopic Isoindolinones Bearing both Central and Axial Chirality DOI Creative Commons

Jun Gu,

Lihong Zhang,

Hongfeng Zhuang

и другие.

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Isotopically chiral molecules have drawn much attention due to their practical applications in drug discovery. However, existing studies this area are mainly limited centrally and H/D exchange. Herein, we report a phosphoric acid-catalyzed atroposelective [4+1] annulation of ketoaldehydes 1H-indol-1-amines. By means strategy, series D- 18O-labeled atropisomers featuring both central axial chiralities synthesized with high enantioselectivities diastereoselectivities good excellent isotopic incorporation. Experimental density functional theory suggest that the reaction involves sequential condensation, cyclization isomerization cascade, which second step is enantio-determining process.

Язык: Английский

Процитировано

1
Remote Copper-Catalyzed Atroposelective Synthesis of N–N Axially Chiral Compounds Bearing Minimally Different Alkyl Groups DOI

Zhaoliang Ge,

Cuiju Zhu,

Guang Xu

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 25, 2025

Herein, we report a copper-catalyzed remote asymmetric [4+1] annulation/aromatization between yne-allylic esters and N-aminoindoles, providing axially chiral N,N'-indolepyrroles that contain sterically comparable ortho substituents, such as methyl ethyl. This reaction proceeds smoothly under mild conditions, affording products with excellent regio- enantioselectivities while demonstrating broad functional group compatibility. The synthetic utility of this approach is further showcased through the late-stage modification biologically relevant scaffolds. Additionally, preliminary mechanistic investigations indicate nucleophilic substitution enantio-determining step.

Язык: Английский

Процитировано

0