Brønsted Acid-Catalyzed, Asymmetric Allenoate Claisen Reaction DOI Creative Commons

Rachael E. Hamilton,

Ellen A. Berkley,

Iain K. Laufer

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 26, 2024

An auxiliary-based protocol is described for an asymmetric allenoate Claisen rearrangement. Silicated tosic acid (10 mol %) was used as inexpensive, user-friendly catalyst. Stereochemical analysis revealed a preferential attack at the

Language: Английский

Planar-chiral arene ruthenium complexes: synthesis, separation of enantiomers, and application for catalytic C–H activation DOI
Mikhail A. Boym, Roman A. Pototskiy, Evgeniya Podyacheva

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(33), P. 4491 - 4494

Published: Jan. 1, 2024

The enantiomers of an arene ruthenium complex were separated by chromatography using auxiliary chiral phosphine. resolved planar-chiral catalyzed asymmetric C–H activation N -methoxy-benzamides.

Language: Английский

Citations

5
H8‐BINOL‐Derived Chiral η6‐Benzene Ligands: New Opportunities for the Ruthenium‐Catalyzed Asymmetric C−H Activation DOI

Junxuan Li,

Guodong Wang,

Weicong Guo

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(31)

Published: April 29, 2024

Abstract Given the tremendous success of (p‐cymene)Ru II ‐catalyzed C−H activation over past 20 years, community has long been aware that development chiral η 6 ‐benzene (Ben) ligands should be a potent strategy for achieving attractive but incredibly underdeveloped ruthenium(II)‐catalyzed asymmetric activation. However, it rarely achieved due to severe difficulty in developing proper Ben ligands. In particular, designing by connecting benzene fragment framework including rings remained an unsolved challenge until this effort. Here we present novel class axially derived from readily available ( S )‐5,5′,6,6′,7,7′,8,8′‐octahydro‐1,1′‐bi‐2‐naphthol (( )‐H 8 ‐BINOL) 4–8 steps. Notably, when coordinated with ruthenium, such ligand containing three only forms one possible isomeric BenRu complexes. The related catalysts could effectively catalyze N‐sulfonyl ketimines alkynes, affording range spirocyclic sultams up 99 % yield >99 ee. These are expected find broad applications future.

Language: Английский

Citations

5
Planar chiral arene ruthenium complexes derived from R-carvone DOI
Mikhail A. Boym, Roman A. Pototskiy, Evgeniya Podyacheva

et al.

Dalton Transactions, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Natural R -carvone was converted into ruthenium complexes with planar-chiral arene ligands. Similar to the classical [(cymene)RuCl 2 ] complex, they catalyse C–H activation reactions, albeit low stereoselectivity.

Language: Английский

Citations

0
Structurally diverse polyketides and alkaloids produced by a plant-derived fungus Penicillium canescens L1 DOI Creative Commons
Wei Wu,

Xun Wei,

Qiong Liao

et al.

Natural Products and Bioprospecting, Journal Year: 2025, Volume and Issue: 15(1)

Published: April 3, 2025

A series of structurally diverse polyketides (1-3), sesterterpenoids (24 and 25), alkaloids (26-34) were isolated from the fermentation a plant-derived fungus Penicillium canescens L1 on solid rice medium. Among these secondary metabolites, penicanesols A-G (1-7) new structures, which elucidated by NMR, HR-ESI-MS, ECD calculation, X-ray diffraction. Penicanesol (1) represented rare dimer derived phthalan derivatives, characterized 5/6/6/6/5 heteropentacyclic core. The bioassay NCI-H1975 cell model showed that two compounds had good cytotoxic activities, most significant activate compound 13 an IC50 value 4.24 ± 0.13 μM, more than positive control drug (12.99 μM).

Language: Английский

Citations

0
Ruthenium catalyst with a planar-chiral arene ligand: synthesis, separation of enantiomers, and application in C-H activation of N-methoxy-benzamides DOI Creative Commons
Mikhail A. Boym, Roman A. Pototskiy, Evgeniya Podyacheva

et al.

Published: Jan. 11, 2024

Heating tert-butyl-tetraline with [(p-cymene)RuCl2]2 produces the racemic complex [(arene)RuCl2]2, which can be separated into enantiomers by chromatography of its diastereomeric adducts chiral phosphine ligand. The resolved catalyzes C-H activation N-methoxy-benzamides and their annulation N-vinyl-pivaloyl amide giving dihydroisoquinolones in 50-90% yields 70:30-90:10 enantiomeric ratio.

Language: Английский

Citations

1
The Difference in Ir-Catalyzed C(sp2)–H and C(sp3)–H Bond Activation Assisted by a Directing Group: Cyclometalation via Cis- or Trans-Chelation? DOI

Ling-Qi Meng,

Jian-Sen Wang,

Xiao-Xia You

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 63(38), P. 17626 - 17638

Published: Sept. 5, 2024

Iridium-catalyzed C-H borylation of aromatic and aliphatic hydrocarbons assisted by a directing group was theoretically investigated. Density functional theory (DFT) calculations revealed both Ir-catalyzed C(sp

Language: Английский

Citations

1
A Chiral Amide Directing Group for Ruthenium-Catalyzed Asymmetric C–H Activation DOI
Dirk Trauner,

Yingfang Wang

Synfacts, Journal Year: 2024, Volume and Issue: 20(03), P. 0318 - 0318

Published: Feb. 14, 2024

Key words asymmetric C–H activation - chiral directing group ruthenium(II) catalysis

Language: Английский

Citations

0
H8‐BINOL‐Derived Chiral η6‐Benzene Ligands: New Opportunities for the Ruthenium‐Catalyzed Asymmetric C−H Activation DOI

Junxuan Li,

Guodong Wang,

Weicong Guo

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(31)

Published: April 29, 2024

Abstract Given the tremendous success of (p‐cymene)Ru II ‐catalyzed C−H activation over past 20 years, community has long been aware that development chiral η 6 ‐benzene (Ben) ligands should be a potent strategy for achieving attractive but incredibly underdeveloped ruthenium(II)‐catalyzed asymmetric activation. However, it rarely achieved due to severe difficulty in developing proper Ben ligands. In particular, designing by connecting benzene fragment framework including rings remained an unsolved challenge until this effort. Here we present novel class axially derived from readily available ( S )‐5,5′,6,6′,7,7′,8,8′‐octahydro‐1,1′‐bi‐2‐naphthol (( )‐H 8 ‐BINOL) 4–8 steps. Notably, when coordinated with ruthenium, such ligand containing three only forms one possible isomeric BenRu complexes. The related catalysts could effectively catalyze N‐sulfonyl ketimines alkynes, affording range spirocyclic sultams up 99 % yield >99 ee. These are expected find broad applications future.

Language: Английский

Citations

0
Sulfoximine Aided Ru(II)-Catalyzed Asymmetric Double C(sp2)–H Hydroarylations of Olefins DOI
Somratan Sau, Koneti Kondalarao,

Paushali Naskar

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 21, 2024

Presented here is a sulfoximine-directed Ru(II)-catalyzed asymmetric intramolecular double C(sp

Language: Английский

Citations

0
Allylation of Lactol in Water DOI
Mengxue Zheng, Wenxiu Gao, Lei Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 20, 2024

We developed a water-promoted cross-coupling of 3-hydroxyisobenzofuran-1(3

Language: Английский

Citations

0