Organocatalytic Asymmetric Synthesis of C‐N Atropisomers with Pyrrole, Oxindole and Succinimide Scaffold DOI
Subhankar Biswas, Snehasis Kundu, Subhas Chandra Pan

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Abstract An asymmetric synthesis of C−N atropisomers with pyrrole, oxindole and succinimide moities was developed via organocatalytic desymmetric Michael addition 3‐pyrrolyloxindole prochiral N‐aryl maleimides. The were obtained in acceptable yields high diastero‐ enantioselectivities (>20 : 1 dr, up to >99 % ee). Rotational energy barrier has also been determined.

Language: Английский

Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field DOI
Hong‐Hao Zhang,

Tian‐Zhen Li,

Si‐Jia Liu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(3)

Published: Nov. 2, 2023

With the rapid development of asymmetric catalysis, demand for enantioselective synthesis complex and diverse molecules with different chiral elements is increasing. Owing to unique features atropisomerism, catalytic atropisomers has attracted a considerable interest from chemical science community. In particular, introducing additional elements, such as carbon centered chirality, heteroatomic planar helical into provides an opportunity incorporate new properties axially compounds, thus expanding potential applications atropisomers. Thus, it important perform transformations synthesize bearing multiple elements. spite challenges in transformations, recent years, chemists have devised powerful strategies under organocatalysis or metal synthesizing wide range enantioenriched Therefore, become emerging field. This review summarizes progress this field indicates challenges, thereby promoting horizon.

Language: Английский

Citations

83
Enantioselective synthesis of molecules with multiple stereogenic elements DOI Creative Commons
Arthur Gaucherand, Expédite Yen‐Pon,

Antoine Domain

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(22), P. 11165 - 11206

Published: Jan. 1, 2024

This review explores the fascinating world of molecules featuring multiple stereogenic elements, unraveling different strategies designed over years for their enantioselective synthesis.

Language: Английский

Citations

17
Enantioselective Synthesis of Axially and Centrally Chiral Styrenes via Nickel-Catalyzed Desymmetric Hydrocyanation of Biaryl Dienes DOI
Can Li,

Song‐Zhou Cai,

Juntao Ye

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3867 - 3871

Published: May 1, 2024

Herein, a highly regio-, enantio-, and diastereoselective nickel-catalyzed desymmetric hydrocyanation of biaryl dienes for the simultaneous construction axial central chiralities is presented, which offers convenient approach to variety tirenes containing union an axially chiral centrally α-chiral nitrile under mild conditions using commercially available catalyst. The synthetic utility highlighted by development novel phosphine ligand biphenyl-based diene their potential applications in field asymmetric catalytic reactions.

Language: Английский

Citations

8
Phosphine-Catalyzed Stereospecific and Enantioselective Desymmetrizative [3+2] Cycloaddition of MBH Carbonates and N-(2-tert-Butylphenyl)maleimides DOI

Jie Hou,

Hao Wei, Ying Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 9068 - 9077

Published: June 1, 2024

Herein, we report an l-valine-derived amide phosphine-catalyzed [3+2] cyclization of MBH carbonates and N-(2-tert-butylphenyl)maleimides via asymmetric desymmetrization. Bicyclic N-aryl succinimide derivatives bearing three continuous chiral centers with a remote C–N atropisomeric chirality were constructed stereospecifically enantioselectively. A wide variety could be employed in this process to deliver highly optically pure moderate excellent yields.

Language: Английский

Citations

7
Recent Advances in the Reaction of MBH Carbonates: Scope and Mechanism DOI
Yifan Shao, Lei Zhang, Xiangtai Meng

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: June 27, 2024

Abstract In recent years, Morita‐Baylis‐Hillman (MBH) carbonates have been extensively used in domino reactions for the synthesis of novel cyclic and acyclic compounds. This review highlights progress made last decade a series compounds from an uncyclized reaction or annulation MBH carbonates, which demonstrates that excellent reactivity high research value as representative substrates organic synthesis. We hope summary understanding can inspire chemists to apply these design more efficient reactions, will be beneficial drug chemistry.

Language: Английский

Citations

7
Recent Advances in Catalytic Desymmetrization for the Synthesis of Axially Chiral Biaryls DOI Creative Commons

Junsoo Moon,

Sangji Kim,

Su Jin Lee

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: June 7, 2024

Abstract Atropisomeric compounds have been discovered in pharmaceuticals and materials science, their enantioselective syntheses gained tremendous attention. Among strategies for catalytic atroposelective synthesis, desymmetrization provides robust straightforward approaches to axially chiral biaryls. Due the relative ease of substrate design compared other strategies, has emerged as a pivotal stage converting fascinating chemistry into its counterpart, despite challenges such formation achiral products by subsequent reactions long distance between reaction site stereogenic axis. This review offers comprehensive overview recent advancements using organo‐ metal catalysts, addressing solutions, aims provide insights future developments this field.

Language: Английский

Citations

5
Catalytic Generation of Remote C–N Axial Chirality through Atroposelectivede novoArene Construction DOI
Subhajit Mondal, Santanu Mukherjee

Organic Letters, Journal Year: 2022, Volume and Issue: 24(45), P. 8300 - 8304

Published: Nov. 4, 2022

The first atroposelective desymmetrization of prochiral N-aryl maleimides through its conversion to axially chiral phthalimides is developed by applying a de novo arene construction strategy. Catalyzed bis(3,5-dimethylphenyl)prolinol TMS-ether, this reaction proceeds oxidative [4 + 2]-cycloaddition with α,β-unsaturated aldehydes generate only C-N axis remote from the sites excellent enantioselectivity (up 97.5:2.5 er).

Language: Английский

Citations

15
Phosphine-Catalyzed Ring-Opening Regioselective Addition of Cyclopropenones with Amides DOI
Huamin Wang,

Yibo Wei,

Yongjun He

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10093 - 10098

Published: June 27, 2024

A series of amides, including α-bromo hydroxamates,

Language: Английский

Citations

3
Direct Access to CF3-Containing 4H-1,3-Oxazines and 2-Aminopyrimidines Via a [4 + 2] Annulation Using In Situ Generated Carbodiimide Anions DOI
Huamin Wang,

Wenjing Niu,

Wei Min

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

The carbodiimide anions which were generated in situ from N-cyano-N-aryl-p-toluenesulfonamides (NCTS) the presence of base participated annulations that remain less reported to date. Herein, we have developed for first time an efficient and environmentally friendly [4 + 2] annulation reaction CF3-substituted hetero-1,3-dienes with NCTS synthesis 4H-1,3-oxazines 2-aminopyrimidines under transition-metal-free conditions. methodology demonstrates advantages readily available substrates, simple operation, good functional group tolerance, broad substrate scope, providing a promising route structurally diverse scaffolds. products followed by transformations provide facile TAS2R14 agonist analogues.

Language: Английский

Citations

0
Highly Enantioselective Organocatalytic Mannich Reaction of α-Benzylidene Succinimides with N-Boc Imines: Experimental and Theoretical Studies DOI

K Kimura,

Yuto Shimizu,

Katsuya Kanno

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

The development of efficient and practical methods for the construction chiral succinimide frameworks, which are backbone various natural products widely studied in field pharmaceuticals, attracts considerable research attention. In this study, an asymmetric Mannich reaction α-benzylidene succinimides with N-Boc imines was successfully performed using a bifunctional squaramide-type organocatalyst derived from quinine, affording corresponding adduct two contiguous stereocenters high yields (up to 98%) diastereoselectivities >20:1 dr) excellent enantioselectivities 99% ee). This protocol provides direct approach prepare derivatives simple starting material. Density Functional Theory (DFT) calculations conformational search autosampling program revealed that enantioselectivity profile dominated by deformation organocatalyst.

Language: Английский

Citations

0