Atroposelective Formal [2 + 5] Macrocyclization Synthesis for a Novel All-Hydrocarbon Cyclo[7] Meta-Benzene Macrocycle DOI Creative Commons
Chao Gao, Hongchen Li, Jing Zhao

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(14), P. 3363 - 3363

Published: July 17, 2024

A novel axially chiral all-hydrocarbon cyclo[7] (1,3-(4,6-dimethyl)benzene (

Pd-catalyzed asymmetric Larock reaction for the atroposelective synthesis of N─N chiral indoles DOI Creative Commons
Jinlei Wang, Deng Pan, Fen Wang

et al.

Science Advances, Journal Year: 2024, Volume and Issue: 10(19)

Published: May 10, 2024

Atropisomeric indoles defined by a N─N axis are an important class of heterocycles in synthetic and medicinal chemistry material sciences. However, they remain heavily underexplored due to limited methods challenging stereocontrol over the short bonds. Here, we report highly atroposelective access axially chiral via asymmetric Larock reaction. This protocol leveraged powerful role phosphoramidite ligand attenuate common dissociation original reaction, forming with excellent functional group tolerance high enantioselectivity palladium-catalyzed intermolecular annulation between readily available o -iodoaniline alkynes. The multifunctionality prepared allowed diverse post-coupling transformations, affording broad array functionalized indoles. Experimental computational studies have been conducted explore reaction mechanism, elucidating enantio-determining rate-limiting steps.

Language: Английский

Citations

8
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
Controlling Stereoselectivity with Noncovalent Interactions in Chiral Phosphoric Acid Organocatalysis DOI
Isaiah O. Betinol, Yutao Kuang,

Brian P. Mulley

et al.

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: March 18, 2025

Chiral phosphoric acids (CPAs) have emerged as highly effective Brønsted acid catalysts in an expanding range of asymmetric transformations, often through novel multifunctional substrate activation modes. Versatile and broadly appealing, these benefit from modular tunable structures, compatibility with additives. Given the unique types noncovalent interactions (NCIs) that can be established between CPAs various reactants─such hydrogen bonding, aromatic interactions, van der Waals forces─it is unsurprising catalyst systems become a promising approach for accessing diverse chiral product outcomes. This review aims to provide in-depth exploration mechanisms by which impart stereoselectivity, positioning NCIs central feature connects broad spectrum catalytic reactions. Spanning literature 2004 2024, it covers nucleophilic additions, radical atroposelective bond formations, highlighting applicability CPA organocatalysis. Special emphasis placed on structural mechanistic features govern CPA-substrate well tools techniques developed enhance our understanding their behavior. In addition emphasizing details stereocontrolling elements individual reactions, we carefully structured this natural progression specifics broader, class-level perspective. Overall, findings underscore critical role catalysis significant contributions advancing synthesis.

Language: Английский

Citations

0
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
Atroposelective Formal [2 + 5] Macrocyclization Synthesis for a Novel All-Hydrocarbon Cyclo[7] Meta-Benzene Macrocycle DOI Creative Commons
Chao Gao, Hongchen Li, Jing Zhao

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(14), P. 3363 - 3363

Published: July 17, 2024

A novel axially chiral all-hydrocarbon cyclo[7] (1,3-(4,6-dimethyl)benzene (

Citations

0