Enantioselective Transformation of Hydrazones via Remote NHC Catalysis: Activation Across C═N and N–N Bonds DOI
Jiamiao Jin,

Ya Lv,

Wenli Tang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 18378 - 18384

Published: Nov. 30, 2024

The catalytic asymmetric transformation of nitrogen atoms to prepare heterocyclic molecules is significant value in organic synthesis and biological applications. Here, we disclose the activation atom hydrazine-derived hydrazone via an N-heterocyclic carbene (NHC) catalyst for highly enantioselective formal cycloaddition reactions. range NHC catalysis extends across several (carbon hetero) diverse chemical bonds (C═N N–N bonds) activate at remote sites with excellent reactivity (stereo)selectivity control. Our strategy activation, along NHC-bound diaza-diene intermediate generated during process, offers alternative solutions synthesis.

Language: Английский

Advances in organocatalytic asymmetric [3 + 3] cycloadditions: synthesis of chiral six-membered (hetero)cyclic compounds DOI

Ziqi Zhu,

Tian‐Zhen Li,

Sijia Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5573 - 5604

Published: Jan. 1, 2024

This review has summarized the development of organocatalytic asymmetric [3 + 3] cycloadditions and given insights into remaining challenges to promote future this field.

Language: Английский

Citations

16
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

12
Catalytic atroposelective synthesis of indolyl quinazolinones bearing N–N/C–C diaxes DOI

Ning‐Yi Wang,

Shuo Gao,

Zhiwei Shu

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

Language: Английский

Citations

1
Enantioconvergent and diastereoselective synthesis of atropisomeric hydrazides bearing a cyclic quaternary stereocenter through ternary catalysis DOI Creative Commons
Xia Wang, Shaojie Wang,

Xiaolan Xin

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(33), P. 13240 - 13249

Published: Jan. 1, 2024

The enantioselective and diastereoselective synthesis of atropisomeric hydrazides with defined vicinal central axial chirality via ternary catalysis in a one-pot process is reported.

Language: Английский

Citations

4
Synthesis of N–N Axially Chiral Pyrrolyl-oxoisoindolin via Isothiourea-Catalyzed Acylative Dynamic Kinetic Resolution DOI

Tongtong Wang,

Jun Cao, Xin Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6179 - 6184

Published: July 18, 2024

The development of methods for the asymmetric synthesis N-N axial chirality remains elusive and challenging. Here, we disclose a method construction axially chiral pyrrolyl-oxoisoindolins along with central via isothiourea (ITU)-catalyzed acylative dynamic kinetic resolution (DKR). Axial was introduced into DKR hemiaminals first time. This protocol features mild conditions excellent yields enantioselectivities.

Language: Английский

Citations

4
Asymmetric construction of axial and planar chirality with N-heterocyclic carbene (NHC) organocatalysis DOI
Meng Zhang,

Xiaoqun Yang,

Xiaolin Peng

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 30, 2024

Language: Английский

Citations

4
Divergent Synthesis of Axially Chiral 2-Pyranones and Fused 2-Pyridones via N-Heterocyclic Carbene-Catalyzed Atroposelective [3 + 3] Annulation DOI
Z. Liu, Chenxing Li,

Simiao Zhang

et al.

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

Published: Jan. 24, 2025

An N-heterocyclic carbene-catalyzed atroposelective [3 + 3] annulation of alkynyl acylazoliums with benzothiazole derivatives has been developed for the divergent synthesis axially chiral triaryl 2-pyranones and fused 2-pyridones. The regioselectivity this protocol depends on structure benzothiazoles three different nucleophilic centers. obtained frameworks represent a new class arylheterocycle atropisomers, which may be potentially useful in medicinal chemistry.

Language: Английский

Citations

0
Organocatalyzed diastereo- and enantioselective synthesis of N–N atropisomeric isoindolinones bearing central chirality DOI Creative Commons
Xingguang Li, Xinning Wang,

Boming Shen

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Feb. 15, 2025

Methods for catalytically constructing of N–N axially chiral scaffolds have garnered significant attention since such compounds are widely present in natural products, bioactive molecules, and organic materials. Herein, we report a highly diastereoselective enantioselective organocatalyzed [4 + 1] annulation method synthesizing diverse valuable isoindolinones that possessing axial central chiralities. This methodology uses phosphoric acid as bifunctional catalyst to promote cascade sequence involving two nucleophilic additions, dehydration, dearomatization processes. Control experiments DFT calculations revealed possible mechanism which the stereoselectivity-determining step is likely involve irreversible formation hydroxy biaryl intermediate. Additionally, preliminary biological activity studies showed some these potential suppressing tumor-cell proliferation. attention. Here, authors

Language: Английский

Citations

0
Asymmetric synthesis of acyclic N–N axially chiral indole compounds via catalytic N-acylation reaction DOI

Zilu Huang,

Yunyi Xu,

Wei Lin

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5437 - 5442

Published: Jan. 1, 2024

Herein, we present an enantioselective synthesis of N -aminoindoles bearing a N–N axis via chiral isothiourea catalyzed asymmetric -acylation. Notably, some the products exhibited promising cytotoxicity activities against cancer cell lines.

Language: Английский

Citations

3
Catalytic Atroposelective Synthesis of N–N Axially Chiral Indolylamides DOI Creative Commons

Tian‐Zhen Li,

Shufang Wu,

Ning‐Yi Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12559 - 12575

Published: Aug. 27, 2024

The catalytic atroposelective synthesis of N–N axially chiral indolylamides was established via dynamic kinetic resolution, which makes use Lewis base-catalyzed asymmetric acylation N-acylaminoindoles as a new type platform molecule with anhydrides. By this strategy, series were synthesized in overall good yields (up to 98%) excellent enantioselectivities 99% ee). Moreover, some these display extent anticancer activity, demonstrates their potential application medicinal chemistry. Therefore, work has not only provided strategy for the monoaryl indoles but also offered member configurational stability and promising application, thereby solving challenges indoles.

Language: Английский

Citations

2