Iridium-Catalyzed Asymmetric Hydroarylation of Unactivated Alkenes with Heterobiaryls: Simultaneous Construction of Axial and Central Chirality DOI
Fei Li, Yicong Luo,

Jinbao Ren

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6835 - 6840

Published: Aug. 7, 2024

There are only a few examples being reported for the simultaneous control of central chirality and axial because it is more challenging. Herein, we report an iridium-catalyzed asymmetric hydroarylation unactivated alkenes with heterobiaryls to simultaneously construct chirality. The reaction showed broad substrate scope delivered products satisfactory results. results experiments demonstrated that FerroLANE ligand promotes proceed along specific modified Chalk-Harrod mechanism.

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

74

Catalytic atroposelective synthesis DOI
Shao‐Hua Xiang, Wei‐Yi Ding, Yong‐Bin Wang

et al.

Nature Catalysis, Journal Year: 2024, Volume and Issue: 7(5), P. 483 - 498

Published: April 30, 2024

Language: Английский

Citations

31

Atroposelective catalysis DOI

Tanno A. Schmidt,

Valeriia Hutskalova,

Christof Sparr

et al.

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: 8(7), P. 497 - 517

Published: June 18, 2024

Language: Английский

Citations

16

Iron-catalyzed stereoselective C–H alkylation for simultaneous construction of C–N axial and C-central chirality DOI Creative Commons
Zijing Zhang,

Nicolas Jacob,

Shilpa Bhatia

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: April 25, 2024

Abstract The assembly of chiral molecules with multiple stereogenic elements is challenging, and, despite indisputable advances, largely limited to toxic, cost-intensive and precious metal catalysts. In sharp contrast, we herein disclose a versatile C–H alkylation using non-toxic, low-cost iron catalyst for the synthesis substituted indoles two elements. key achieving excellent diastereo- enantioselectivity was substitution on N -heterocyclic carbene ligand providing steric hindrance extra represented by noncovalent interaction concomitant generation C–N axial chirality C -stereogenic center. Experimental computational mechanistic studies have unraveled origin catalytic efficacy stereoselectivity.

Language: Английский

Citations

8

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

Recent advances in organocatalytic atroposelective reactions DOI Creative Commons

Henrich Szabados,

Radovan Šebesta

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 55 - 121

Published: Jan. 9, 2025

Axial chirality is present in a variety of naturally occurring compounds, and becoming increasingly relevant also medicine. Many axially chiral compounds are important as catalysts asymmetric catalysis or have chiroptical properties. This review overviews recent progress the synthesis via organocatalysis. Atroposelective organocatalytic reactions discussed according to dominant catalyst activation mode. For covalent organocatalysis, typical enamine iminium modes presented, followed by N -heterocyclic carbene-catalyzed reactions. The bulk devoted non-covalent activation, where Brønsted acids feature most prolific catalytic structure. last part article discusses hydrogen-bond-donating other motifs such phase-transfer catalysts.

Language: Английский

Citations

1

Simultaneous construction of inherent and axial chirality by cobalt-catalyzed enantioselective C-H activation of calix[4]arenes DOI Creative Commons
Tong Li, Yanbo Zhang, Cong Du

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Sept. 3, 2024

Language: Английский

Citations

6

Catalytic stereodivergent and simultaneous construction of axial and point chirality DOI
Wentao Wang, Sen Zhang,

Wenxuan Lin

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(12), P. 3308 - 3319

Published: Jan. 1, 2024

An unprecedented ligand-enabled stereodivergent construction of both N–N axial and point chirality in a single step is reported.

Language: Английский

Citations

5

Double cobalt-catalyzed atroposelective C–H activation: One-step synthesis of atropisomeric indoles bearing vicinal C–C and C–N diaxes DOI Creative Commons

Amandine Luc,

João C. A. Oliveira, Philipp Boos

et al.

Chem Catalysis, Journal Year: 2023, Volume and Issue: 3(10), P. 100765 - 100765

Published: Sept. 26, 2023

Language: Английский

Citations

11

Enantioselective Construction of Indolizines Containing Vicinal Diaxial Chirality DOI

Yongjian Yang,

Chuanyao Yang,

Xingcan Zhang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3442 - 3450

Published: Feb. 12, 2025

Language: Английский

Citations

0