Palladium-Catalyzed Enantioselective β-Hydride Elimination for the Construction of Remote Stereocenters DOI Creative Commons
Weiwei Zi, Shaozi Sun, Shengnan Sun

и другие.

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Ноя. 21, 2024

Abstract The β-H elimination is a crucial elementary step in transition-metal catalysis, but controlling the stereochemistry of this process has been underdeveloped. limited works reported so far have only focused on creating axial chirality allenes, and no report able to build central using asymmetric elimination. In study, we Trost ligand-enabled enantioselective desymmetric reaction from π-allyl-Pd. This transformation provides rapid access cyclohexenes bearing C4-remoted stereocenter, total synthesis (-)-oleuropeic acid (-)-7-hydroxylterpineol was demonstrated. Computational studies shown that rate-determining step, non-covalent interactions between amide moiety ligand benzene cyclohexane moieties substrate play key role stereocontrol during

Язык: Английский

Enantioselective Synthesis of Axially Chiral Alkylidenecycloalkanes via Copper-Catalyzed Functionalization of Acyl Allenols DOI

Baihui Gong,

Qing‐Bin Lu,

R. Li-jiun Sun

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 2351 - 2358

Опубликована: Янв. 24, 2025

Язык: Английский

Процитировано

3
Organocatalytic Atroposelective Fluorooxindole Addition to Coumarin Michael Acceptors DOI Creative Commons
Maria Bouda,

Grace E. Hana,

Dea Xhili

и другие.

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Organocatalytic atropisomeric synthesis with fluorinated oxindoles and 4-halo-3-nitrocoumarins gives congested structures displaying a Csp2-Csp3 chirality axis an adjacent tetrasubstituted stereogenic carbon center good yields, up to 97% ee 41 : 1 dr. The scalable dehalogenative C-C bond formation is achieved under mild conditions commercially available urea catalyst.

Язык: Английский

Процитировано

2
Palladium-catalyzed enantioselective β-hydride elimination for the construction of remote stereocenters DOI Creative Commons
Shaozi Sun, Shengnan Sun, Weiwei Zi

и другие.

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Март 5, 2025

The β-H elimination is a crucial elementary step in transition-metal catalysis, but controlling the stereochemistry of this process has been underdeveloped. limited works reported so far have only focused on creating axial chirality allenes, and no report able to build central using asymmetric elimination. In study, we Trost ligand-enabled enantioselective desymmetric reaction from π-allyl-Pd. This transformation provides rapid access cyclohexenes bearing C4-remoted stereocenter, total synthesis (-)-oleuropeic acid (-)-7-hydroxyterpineol demonstrated. Computational studies shown that rate-determining step, non-covalent interactions between amide moiety ligand benzene cyclohexane moieties substrate play key role stereocontrol during

Язык: Английский

Процитировано

1
Cu-catalyzed enantioselective assembly of axially chiral allylic boronates DOI
Shuai Wang, Jianbo Liu,

Wenyue Ma

и другие.

Science China Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 25, 2024

Язык: Английский

Процитировано

4
Phosphoric Acid-Catalyzed Enantioselective Synthesis of Axially Chiral Cyclobutanamides DOI

Guang Cheng,

Jinfeng Zheng,

Yilin Zhu

и другие.

Organic Letters, Год журнала: 2025, Номер 27(10), С. 2509 - 2514

Опубликована: Март 5, 2025

Chiral cyclobutanamide is a privileged scaffold in drug discovery. Here, we describe, for the first time, synthesis of axially chiral cyclobutanamides via phosphoric acid-catalyzed enantioselective condensation between N-arylcarbamyl cyclobutanones and hydroxylamines. Rational substrate design, incorporating an amide moiety (CONHR) into cyclobutanone backbone formation multi-hydrogen bonding network involving N-H this portion, responsible excellent enantioselectivity achieved stereodetermining dehydration process, which supported by detailed mechanistic study.

Язык: Английский

Процитировано

0
Rh(I)-Catalyzed Modular Synthesis of Axially Chiral Alkylidene Azacycloalkanes DOI Creative Commons
Yang Chen, Jiayan Chen, Shifa Zhu

и другие.

ACS Central Science, Год журнала: 2025, Номер unknown

Опубликована: Май 11, 2025

Язык: Английский

Процитировано

0
Ligand-controlled regiodivergent arylation of aryl(alkyl)alkynes and asymmetric synthesis of axially chiral 9-alkylidene-9,10-dihydroanthracenes DOI Creative Commons
Chao Sun, Ting Qi, Faiz‐Ur Rahman

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Окт. 29, 2024

Transition metal-catalyzed addition of organometallics to aryl(alkyl)alkynes has been well known proceed with the regioselectivity in forming a carbon-carbon bond at alkyl-substituted carbon (β-addition). Herein, reverse regiochemistry high selectivity giving 1,1-diarylalkenes (α-addition) was realized reaction arylboronic acids by use rhodium catalyst coordinated chiral diene ligand, whereas arylation same alkynes proceeded usual (β-addition) presence rhodium/DM-BINAP catalyst. The can be switched choice ligands on catalysts. This also enabled catalytic asymmetric synthesis phoenix-like axially alkylidene dihydroanthracenes enantioselectivity through an α-addition/1,4-migration/cyclization sequence.

Язык: Английский

Процитировано

2
Enantioselective Synthesis of Axially Chiral Silacyclohexylidene Oxime Ethers by Chiral Phosphoric Acid Catalysis DOI
Xiyu Wang, Xingang Xie, Zhongwei Wu

и другие.

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Окт. 17, 2024

Abstract The first asymmetric condensation of prochiral silacyclohexanones with hydroxylamines by chiral phosphoric acid catalysis has been developed, which provides a facile and straightforward protocol for the enantioselective construction valuable axially silacyclohexylidene oxime ethers that are otherwise inaccessible. Notably, this constitutes rare example accessing silacycles featuring axial chirality.

Язык: Английский

Процитировано

0
Palladium-Catalyzed Enantioselective β-Hydride Elimination for the Construction of Remote Stereocenters DOI Creative Commons
Weiwei Zi, Shaozi Sun, Shengnan Sun

и другие.

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Ноя. 21, 2024

Abstract The β-H elimination is a crucial elementary step in transition-metal catalysis, but controlling the stereochemistry of this process has been underdeveloped. limited works reported so far have only focused on creating axial chirality allenes, and no report able to build central using asymmetric elimination. In study, we Trost ligand-enabled enantioselective desymmetric reaction from π-allyl-Pd. This transformation provides rapid access cyclohexenes bearing C4-remoted stereocenter, total synthesis (-)-oleuropeic acid (-)-7-hydroxylterpineol was demonstrated. Computational studies shown that rate-determining step, non-covalent interactions between amide moiety ligand benzene cyclohexane moieties substrate play key role stereocontrol during

Язык: Английский

Процитировано

0