Catalytic Enantioselective Access to Planar‐Chiral Macrocyclophanes

The Chemical Record, Год журнала: 2025, Номер unknown

Опубликована: Май 29, 2025

Macrocyclophanes are a class of macrocyclic molecules featuring aliphatic ansa chains linking non‐adjacent positions an aromatic ring, which have garnered significant attention due to their extensive applications in biological activity, pharmaceutical research, and selective optical recognition. In this review, it summarizes recent advancements the catalytic enantioselective synthesis planar‐chiral macrocyclophanes, focusing on various synthetic routes, including: a) transition‐metal‐catalyzed alkyne cyclotrimerization for planar construction; b) (dynamic) kinetic resolution achiral or prochiral macrocyclophanes; c) substitution rings; d) macrocyclization formation chains. The aim is highlight state‐of‐the‐art advances construction macrocyclophanes push field toward new horizons.

Язык: Английский

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Kinetic Resolution of a Planar–Chiral [2.2]Paracyclophane via Michael Addition to Nitroolefins Catalyzed by N‐Terminal Guanidinylated Helical Peptide

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(16)

Опубликована: Фев. 27, 2024

Abstract Kinetic resolution of 4‐(2‐nitrovinyl)[2.2]paracyclophane based on N‐terminal–guanidinylated resin–bound helical peptide catalyzed asymmetric Michael addition malonate esters was developed. This approach provides a new pathway to enantiopure paracyclophane derivatives characterized by both planar and central chirality, along with the recovery chiral substrate selectivity factor up 111. Additionally, synthetic potential resulting products has been showcased through their successful transformation into β‐substituted γ‐aminobutyric acid.

Язык: Английский

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Recent Advances on Catalytic Atroposelective Synthesis of Planar‐Chiral Macrocycles

Angewandte Chemie, Год журнала: 2024, Номер 136(42)

Опубликована: Авг. 6, 2024

Abstract Planar‐chiral skeletons widely exist in natural products, bioactive compounds, and other functional molecules. Although significant progress has been made the field of asymmetric synthesis centrally or axially chiral molecules over past years, enantioselective constructing planar chirality is still a big obstacle numerous efforts have this field. Previous works mainly focused on assembly planar‐chiral [2,2]‐paracyclophanes metallocenes. This Minireview describes recent advancements catalytic macrocycles, including ansa chain construction, plane formation transformation strategies. It anticipated that will sever as source inspiration for developing new unconventional procedures access to skeletons.

Язык: Английский

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Recent advances toward the catalytic enantioselective synthesis of planar chiral cyclophanes

Chinese Chemical Letters, Год журнала: 2024, Номер 36(7), С. 110678 - 110678

Опубликована: Ноя. 26, 2024

Язык: Английский

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