Asymmetric Synthesis of Benzofuranones with a C3 Quaternary Center via an Addition/Cyclization Cascade Using Noncovalent N-Heterocyclic Carbene Catalysis DOI

Ujjwal Maji,

Supriyo Das,

Arpita Baidya

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Окт. 3, 2024

An asymmetric addition/cyclization cascade of amidoesters and iminoquinones is developed using noncovalent N-heterocyclic carbene (NHC) catalysis. The process enables access to various functionalized benzofuranones with an all-carbon quaternary stereocenter high yields ee values. reaction displays a broad substrate scope. Via product modifications, enantioenriched synthesis biologically relevant spirocyclic lactones lactams achieved. Substrate activation via interaction NHC suggested for the process.

Язык: Английский

N-Heterocyclic carbene (NHC) organocatalysis: from fundamentals to frontiers DOI
Sukriyo Chakraborty,

Soumen Barik,

Akkattu T. Biju

и другие.

Chemical Society Reviews, Год журнала: 2024, Номер unknown

Опубликована: Дек. 18, 2024

This tutorial review provides an overview of various important structural features and reactivity modes NHCs delves deep into the recent advances in NHC-organocatalysis.

Язык: Английский

Процитировано

3
Bifunctional NHC-Catalyzed Asymmetric Intramolecular Conjugate Addition via Noncovalent Interaction DOI

Ujjwal Maji,

Arpita Baidya,

Supriyo Das

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 28, 2025

Herein, we report a novel squaramide containing chiral bifunctional N-heterocyclic carbene (NHC) and its utilization in developing asymmetric intramolecular conjugate addition involving noncovalent interaction. Via concomitant activation of both electrophilic nucleophilic centers substrates, the reaction proceeds through well-organized transition state, thereby affording products with up to 94% ee broad scope. The process is found be scalable. initial mechanistic study supports nature newly designed NHC.

Язык: Английский

Процитировано

0
Desymmetric esterification catalysed by bifunctional chiral N-heterocyclic carbenes provides access to inherently chiral calix[4]arenes DOI Creative Commons
Vojtěch Dočekal, Ladislav Lóška,

Adam Kurčina

и другие.

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Май 13, 2025

Язык: Английский

Процитировано

0
Asymmetric Synthesis of Benzofuranones with a C3 Quaternary Center via an Addition/Cyclization Cascade Using Noncovalent N-Heterocyclic Carbene Catalysis DOI

Ujjwal Maji,

Supriyo Das,

Arpita Baidya

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Окт. 3, 2024

An asymmetric addition/cyclization cascade of amidoesters and iminoquinones is developed using noncovalent N-heterocyclic carbene (NHC) catalysis. The process enables access to various functionalized benzofuranones with an all-carbon quaternary stereocenter high yields ee values. reaction displays a broad substrate scope. Via product modifications, enantioenriched synthesis biologically relevant spirocyclic lactones lactams achieved. Substrate activation via interaction NHC suggested for the process.

Язык: Английский

Процитировано

2