α‐Azaaryl carbonyl derivatives in stereodivergent catalytic reactions DOI Creative Commons

Inwoo Song,

Byungjun Kim,

Hooseung Lee

и другие.

Bulletin of the Korean Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Июнь 4, 2025

Abstract The catalytic synthesis of chiral azaarenes has become a focal point research due to their signifi`1cant applications across various fields, including medicinal chemistry and materials science. α‐Azaaryl carbonyl compounds, featuring both an electron‐withdrawing C=N moiety within azaarene core functional group, have proven be versatile precursors in the stereochemically intricate azaaryl molecules. In particular, generation α‐azaaryl enolate intermediates, catalyzed by Lewis acids, enabled precise construction α‐stereogenic azaarenes. This review explores recent advances stereodivergent transformations derivatives with array carbon electrophiles, emphasizing efficiency systems involving copper acids combined Ir, Pd, Ni, amine, or Ru catalysts. These strategies offer control over stereochemical outcome, facilitating access all stereoisomers multi‐stereogenic Additionally, we discuss sequence‐dependent approach that allows for controlled stereodivergence reactions derivatives. Through detailed exploration advancements, mechanistic insights, practical applications, this underscores potential unlock new avenues compounds. By presenting diverse expanding opportunities controlling stereochemistry, it fosters further development design structurally complex azaarene‐based frameworks.

Язык: Английский

Stereodivergent Ruthenium/Copper Relay Catalysis for Modular Access to δ-Lactones with Two Nonadjacent Carbon Stereocenters DOI

G D Song,

Ruiyan Sun, Xia Liu

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 6, 2025

The stereodivergent synthesis of δ-lactones, which are prevalent in natural product frameworks, from simple starting materials via a single transformation remains significant challenge. Herein, we report an enantio- and diastereodivergent cascade reaction for the modular chiral δ-lactones bearing two nonadjacent quaternary tertiary carbon stereocenters. This approach employs bimetallic Ru/Cu relay catalysis between allylic alcohols azaaryl acetates. method integrates Ru-catalyzed asymmetric borrowing hydrogen reaction, Cu-catalyzed Michael addition, rapid lactonization into one-pot process, with all catalysts substrates introduced at outset. By orthogonal permutation metal catalysts, precise control over relative absolute configurations newly formed stereocenters is achieved, allowing selective access to stereoisomers δ-lactone products predictable efficient manner.

Язык: Английский

Процитировано

0
α‐Azaaryl carbonyl derivatives in stereodivergent catalytic reactions DOI Creative Commons

Inwoo Song,

Byungjun Kim,

Hooseung Lee

и другие.

Bulletin of the Korean Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Июнь 4, 2025

Abstract The catalytic synthesis of chiral azaarenes has become a focal point research due to their signifi`1cant applications across various fields, including medicinal chemistry and materials science. α‐Azaaryl carbonyl compounds, featuring both an electron‐withdrawing C=N moiety within azaarene core functional group, have proven be versatile precursors in the stereochemically intricate azaaryl molecules. In particular, generation α‐azaaryl enolate intermediates, catalyzed by Lewis acids, enabled precise construction α‐stereogenic azaarenes. This review explores recent advances stereodivergent transformations derivatives with array carbon electrophiles, emphasizing efficiency systems involving copper acids combined Ir, Pd, Ni, amine, or Ru catalysts. These strategies offer control over stereochemical outcome, facilitating access all stereoisomers multi‐stereogenic Additionally, we discuss sequence‐dependent approach that allows for controlled stereodivergence reactions derivatives. Through detailed exploration advancements, mechanistic insights, practical applications, this underscores potential unlock new avenues compounds. By presenting diverse expanding opportunities controlling stereochemistry, it fosters further development design structurally complex azaarene‐based frameworks.

Язык: Английский

Процитировано

0