Enhancing the Efficacy of Chiral Ligands and Catalysts: Siloxane-Substituted Oxazoline Ferrocenes as Next-Generation Candidates DOI Creative Commons
Li Dai, Zhao Li, Di Xu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(5), P. 968 - 968

Published: Feb. 22, 2024

Since the discovery of classical chiral oxazoline ferrocene ligands in 1995, they have become pivotal transition metal-catalyzed asymmetric transformations. Over past decade, a notable evolution has been observed with emergence siloxane-substituted ferrocenes, demonstrating significant potential as and catalysts. These compounds consistently delivered exceptional results diverse mechanistically distinct transformations, surpassing capabilities ligands. This review meticulously delineates research progress on compounds. It encompasses synthesis crucial precursors desired products, highlights their achievements catalysis reactions, delves into exploration derivatization these compounds, emphasizing introduction ionophilic groups impact recovery metal In addition to presenting current state knowledge, this propels future directions by identifying topics for further investigation concerning siloxane-tagged derivatives. derivatives are poised be promising candidates next generation highly efficient

Language: Английский

α,α-Difluorinated Allylsulfones: gem-Difluoroethylenyl Reagents for Synthesis of Fluorinated Chiral α-Quaternary Amino Acids DOI
Xiang Huang, Dongmei Fang, Xihong Wang

et al.

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

Published: March 25, 2025

Among numerous fluorine-containing molecules, chiral gem-difluoroethylenes (C═CF2) exhibited unique properties in agrochemicals, pharmaceuticals, and materials science. However, the general synthetic methods were limited to functionalization/defluorination of trifluoromethylalkenes. Here, we disclose a new type difluoroethylenyl reagent, α,α-difluoro allylsulfones, which allows highly enantioselective Cu-catalyzed desulfonylative SN2′ substitution with benzylideneamino esters. This protocol presents novel strategy for construction diversified α-quaternary amino acid derivatives containing gem-difluoroethylene moiety excellent results (up 86% yield, generally 90–98% ee). The ease synthesis applications this protocol, transformations products revealed potential utility chemistry.

Language: Английский

Citations

0

Pd-Catalyzed Enantioselective Creation of All-Carbon Quaternary Center with 2,3-Allenylic Carbonates DOI
Jie Lin, Minqiang Jia, Xu Song

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2349 - 2353

Published: March 15, 2024

Enantioselective construction of all-carbon quaternary centers has been achieved via the palladium-catalyzed highly enantioselective allenylation oxindoles with 2,3-allenylic carbonates to afford a variety optically active allene products, which contain oxindole units different functional groups, in high ee. The corresponding synthetic applications have also demonstrated.

Language: Английский

Citations

3

A General Enantioselective α-Alkyl Amino Acid Derivatives Synthesis Enabled by Cobalt-Catalyzed Reductive Addition DOI

Chengxi Zhang,

Xianqing Wu, Jingping Qü

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 12, 2024

Enantioenriched unnatural amino acids represent a prevalent motif in organic chemistry, with profound applications biochemistry, medicinal and materials science. Herein, we report cobalt-catalyzed aza-Barbier reaction of dehydroglycines unactivated alkyl halides to afford α-amino esters high enantioselectivity. This catalytic reductive alkylative addition protocol circumvents the use moisture-, air-sensitive organometallic reagents, stoichiometric chiral auxiliaries, enabling conversion variety primary, secondary, even tertiary α-alkyl-amino under mild conditions, thus leading broad functional group tolerance. The expedient access biologically active motifs demonstrates practicality this by reducing number synthetic steps enhancing efficiency.

Language: Английский

Citations

3

Asymmetric α-Allylation of N-Unprotected Amino Acid Esters with 1,3-Disubstituted Allyl Acetates Enabled by Chiral-Aldehyde/Palladium Catalysis DOI
Zhou Qing, Zhi-Wei Yin,

Zhu‐Lian Wu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(31), P. 5790 - 5794

Published: July 31, 2023

A chiral aldehyde/palladium catalysis-enabled asymmetric α-allylation of NH2-unprotected amino acid esters with 1,3-disubstituted allyl acetates is described in this work. With the utilization different phosphine ligands, both anti- and syn-selective allylation reactions are achieved enantioselectively. series α,α-disubstituted bearing two adjacent centers produced moderate-to-excellent yields, diastereoselectivities, enantioselectivities.

Language: Английский

Citations

7

Enhancing the Efficacy of Chiral Ligands and Catalysts: Siloxane-Substituted Oxazoline Ferrocenes as Next-Generation Candidates DOI Creative Commons
Li Dai, Zhao Li, Di Xu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(5), P. 968 - 968

Published: Feb. 22, 2024

Since the discovery of classical chiral oxazoline ferrocene ligands in 1995, they have become pivotal transition metal-catalyzed asymmetric transformations. Over past decade, a notable evolution has been observed with emergence siloxane-substituted ferrocenes, demonstrating significant potential as and catalysts. These compounds consistently delivered exceptional results diverse mechanistically distinct transformations, surpassing capabilities ligands. This review meticulously delineates research progress on compounds. It encompasses synthesis crucial precursors desired products, highlights their achievements catalysis reactions, delves into exploration derivatization these compounds, emphasizing introduction ionophilic groups impact recovery metal In addition to presenting current state knowledge, this propels future directions by identifying topics for further investigation concerning siloxane-tagged derivatives. derivatives are poised be promising candidates next generation highly efficient

Language: Английский

Citations

2