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

Dynamic Kinetic Reductive Grignard-Type Addition for the Construction of Axial and Central Chirality DOI

Ya-Ping Shao,

Yong‐Min Liang

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 1147 - 1157

Published: Jan. 3, 2025

This study describes a photoredox/cobalt dual-catalyzed asymmetric Grignard-type addition reaction, enabling the synthesis of axially chiral hexatomic (six–six) N-heterobiaryls bearing extra secondary alcohol unit via an efficient dynamic kinetic transformation racemic N-heterobiaryl triflate substrates. The conversion facilitated both photoredox and classical reductive reaction conditions exhibits good functional group tolerance, broad substrate scope, satisfactory stereoselectivity. Furthermore, control experiments density theory calculations provide preliminary mechanistic insights.

Language: Английский

Citations

3
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

13
An Aza-Enolate Strategy Enables Iridium-Catalyzed Enantioselective Hydroalkenylations of Minimally Polarized Alkenes en Route to Complex N-Aryl β2-Amino Acids DOI Creative Commons

Fenglin Hong,

Craig M. Robertson, John F. Bower

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(33), P. 22923 - 22929

Published: Aug. 6, 2024

Cationic Ir(I)-complexes modified with homochiral diphosphines promote the hydroalkenylative cross-coupling of β-(arylamino)acrylates monosubstituted styrenes and α-olefins. The processes are dependent on presence an NH unit, it is postulated that metalation this generates iridium aza-enolate engages alkene during C-C bond forming event. method offers high branched selectivity enantioselectivity occurs complete atom economy. Diastereocontrolled reduction products provides β

Language: Английский

Citations

4
The influence of acid additive on linear and branch selectivity in the C−H alkylation of the N-pyridinecarbonyl protected 2-methylbenzylamine with 1-heptene catalyzed by Rh2(OAc)4: a theoretical investigation DOI

Lingli Han,

Fei Guan,

Zifan Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The role of an acid additive and the origins reaction are clarified through our calculations.

Language: Английский

Citations

0
Rhodium-Catalyzed Atroposelective C–H Alkylation of 1-Aryl Isoquinoline Derivatives with Cyclopropanols DOI
Wenwen Zhang, Quannan Wang, Chao Zheng

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4017 - 4024

Published: Feb. 20, 2025

Language: Английский

Citations

0
Access to distal biaxial atropisomers by iridium catalyzed asymmetric C–H alkylation DOI Creative Commons
Xueqing Hu,

Yunxu Zhao,

Tong He

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(33), P. 13541 - 13549

Published: Jan. 1, 2024

Herein, we report an iridium-catalyzed asymmetric C–H activation combined with a desymmetrization strategy for synthesizing distal biaxial atropisomers excellent stereoselectivity, displaying promising photophysical and chiroptical properties.

Language: Английский

Citations

3
Diastereodivergent Parallel Kinetic Resolution of Racemic 2-Substituted Pyrrolidines via Iridium-Catalyzed C(sp3)–H Borylation DOI
Maosheng He, Liangjun Xie, Lili Chen

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 18701 - 18707

Published: Dec. 8, 2024

Chiral 2,5-disubstituted pyrrolidines are ubiquitous subunits in natural products, bioactive compounds, pharmaceuticals, and chiral catalysts. However, their asymmetric synthesis still presents a formidable challenge. We herein report rare example of diastereodivergent parallel kinetic resolution racemic 2-substituted via C(sp3)–H borylation. A vast array enantioenriched cis- trans-2,5-disubstituted were obtained with high enantioselectivities. The synthetic utility was demonstrated by downstream transformations, including the optically active pyrrolidine 197B cis-pyrrolidine 225H.

Language: Английский

Citations

1
Directed C–H Alkylation of Heterobiaryls via Iridium Catalysis DOI
Mark Lautens, Ramon Arora

Synfacts, Journal Year: 2024, Volume and Issue: 20(07), P. 0714 - 0714

Published: June 14, 2024

Key words iridium catalysis - atroposelectivity C–H functionalization regioselectivity

Language: Английский

Citations

0
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

Citations

0