Rhodium(II)‐Catalyzed Denitrogenative Transformations of N‐Sulfonyl‐1,2,3‐triazoles DOI
Fatemeh Doraghi,

Mohammad Hossein Morshedsolouk,

Samaneh Ghofrani

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 21, 2024

Abstract N ‐Sulfonyl‐1,2,3‐triazoles are valuable precursors for the generation of α‐imino carbene intermediates in presence metal catalysts, especially rhodium(II) complexes. Due to electrophilic and nucleophilic nitrogen, these reactive can easily be incorporated into many annulations, cycloadditions, C−H or O/N/S−H bond insertions functionalization reactions. A large number pharmaceutically important nitrogen‐based building blocks constructed via this direct atom‐economical strategy. In review, we have described transformations ‐sulfonyl‐1,2,3‐triazoles based on intermediates.

Язык: Английский

Synergistic catalysis for stereocontrol of prochiral nucleophiles in palladium-catalyzed asymmetric allylic substitution DOI
Xi Wang,

Youbin Peng,

Ling Zhao

и другие.

Science China Chemistry, Год журнала: 2023, Номер 66(8), С. 2238 - 2255

Опубликована: Июль 20, 2023

Язык: Английский

Процитировано

19

Catalytic Stereoselective 1,2-cis-Furanosylations Enabled by Enynal-Derived Copper Carbenes DOI
Bidhan Ghosh,

Adam Alber,

Chance Lander

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(2), С. 1037 - 1049

Опубликована: Янв. 8, 2024

1,2-cis-Furanosides are present in various biomedically relevant glycosides, and their stereoselective synthesis remains a significant challenge. In this vein, we have developed approach to 1,2-cis-furanosylations using earth-abundant copper catalysis. This protocol proceeds under mild conditions at room temperature employs readily accessible benchtop stable enynal-derived furanose donors. chemistry accommodates variety of alcohols, including primary, secondary, tertiary, as well mannosyl alcohol acceptors, which been incompatible with most known methods furanosylation. The resulting 1,2-cis-furanoside products exhibit high yields anomeric selectivity both the ribose arabinose series. Furthermore, is independent C2 oxygen-protecting group configuration starting donor. Experimental evidence computational studies support our hypothesis that chelation between oxygen donor an incoming nucleophile responsible for observed 1,2-cis-stereoselectivity.

Язык: Английский

Процитировано

6

Overview of Transition Metal Catalyzed Multicomponent Reactions Based on Trapping of Allylic Electrophiles DOI

Kriti Gupta,

Mahesh Singh Harariya,

Arushi Tyagi

и другие.

ChemCatChem, Год журнала: 2024, Номер 16(4)

Опубликована: Янв. 11, 2024

Abstract Multicomponent reactions provide an excellent approach toward quaternary carbon centres utilizing convergent chemical in a highly selective manner under one‐pot conditions. The reactivity of substrates and metal catalysts is carefully controlled, precluding the formation side‐products. In this context, transition catalyzed onium ylides generated via diazo precursors nucleophiles with third component (an electrophile) have garnered significant attention. Using allylic precursor as electrophilic partner provides opportunities to construct all‐carbon centres. Furthermore, presence allyl fragment multicomponent product serves pivotal handle for carrying out subsequent modifications. Several recent studies employed Rh, Pd, dual Rh/Pd catalytic systems involving alkylation that proceed synergistic or relay pathway. Although not significantly successful, few cases, asymmetric induction achieved through chiral phosphoric acids phosphine ligands. Limited substrate catalyst scope underlying mechanistic complexities posed formidable challenges, slowing advancement reactions. This review details using readily available like compounds, carbonates, (R‐OH, R‐NH 2 , etc .) forming complex organic compounds. Our primary objective discuss issues may facilitate progress field.

Язык: Английский

Процитировано

6

Catalytic Orthogonal Glycosylation Enabled by Enynal‐Derived Copper Carbenes DOI
Surya Pratap Singh, Bidhan Ghosh, Indrajeet Sharma

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(8), С. 1847 - 1856

Опубликована: Фев. 17, 2024

Abstract Herein, we present an approach for catalytic orthogonal glycosylation utilizing earth‐abundant copper carbenes. This method operates under mild conditions and employs readily accessible starting materials, including benchtop stable enynal‐derived glycosyl donors, synthesized at the gram scale. The reaction accommodates a variety of acceptors, primary, secondary, tertiary alcohols. carbenes exhibit remarkable reactivity selectivity, allowing formation glycosidic linkages with different protecting groups stereochemical patterns. provides access to both 1,2‐ cis ‐ trans ‐glycosidic linkages. product stereoselectivity is independent anomeric configuration donor, which also has widely used alkynes thioglycoside donors. An iterative synthesis trisaccharide further demonstrates application this reactivity.

Язык: Английский

Процитировано

4

CuX Dual Catalysis: Construction of Oxazolo[2,3-b][1,3]oxazines via a Tandem CuAAC/Ring Cleavage/[4+2+3] Annulation Reaction DOI

Xiai Luo,

Zhong‐Tao Yang,

Jia Zheng

и другие.

Organic Letters, Год журнала: 2022, Номер 24(40), С. 7300 - 7304

Опубликована: Сен. 30, 2022

CuX as a simple dual catalyst strategy that promotes the tandem transformations of fused oxazolo[2,3-b][1,3]oxazines has been developed. Copper catalyzed terminal ynones, sulfonyl azides, and nitriles for CuAAC/ring cleavage/[4+2] annulation reaction, while halogen ring cleavage [2+3] oxiranes to form final products. This study provides four-component, one-pot synthesizing complex heterocycles from ingredients expands application CuAAC in organic synthesis.

Язык: Английский

Процитировано

9

Rh(II)/Pd(0) Dual Catalysis: Interception of Ammonium Ylide with Allyl Palladium to Construct 2,2-Disubstituted Tetrahydroquinoline Derivatives DOI
Mingxi Du, Xueying Wang, Jie Zhang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(13), С. 9496 - 9504

Опубликована: Июнь 10, 2023

New synthetic methods to construct 2,2-disubstituted tetrahydroquinoline derivatives are of significant value in pharmaceutical chemistry. Herein, a Rh(II)/Pd(0) dual-catalyzed diazo α-aminoallylation reaction has been developed between allylpalladium(II) and ammonium ylides derived from the Rh2(OAc)4-mediated intramolecular N-H bond insertion compounds, affording various good yields up 93% with high chemoselectivities under mild conditions. A substrate scope investigation reveals broad ester substituent tolerance, control experiments provide basis for proposed mechanism.

Язык: Английский

Процитировано

5

Synergistic Rh(II)- and Zn(II)-Catalyzed [3 + 3] Annulation of Diazoenals and α-Hydroxy Ketones for the Direct Synthesis of 2H-Pyrans, A Gateway Toward γ-Pyrones DOI
Pratap Kumar Mandal, Sreenivas Katukojvala

Organic Letters, Год журнала: 2024, Номер 26(43), С. 9227 - 9232

Опубликована: Окт. 21, 2024

A new synergistic Rh(II)/Zn(II)-catalyzed [3 + 3] annulation has been developed between diazoenals and α-hydroxy ketones enabling the direct synthesis of 4-formyl-2H-pyrans. The reaction involves formation protic oxonium ylides from highly electrophilic Rh-enalcarbenoids followed by Zn-templated regioselective intramolecular aldol condensation. Subsequent investigations demonstrated that 4-formyl-2H-pyrans are unique precursors γ-pyrones. γ-pyrones were obtained via Et3N-mediated oxidative deformylation. Further, triflic-acid-promoted double Schmidt provides synthetically important carboxamide-substituted 4-cyano 2H-pyrans.

Язык: Английский

Процитировано

1

Rhodium(II)‐Catalyzed Denitrogenative Transformations of N‐Sulfonyl‐1,2,3‐triazoles DOI
Fatemeh Doraghi,

Mohammad Hossein Morshedsolouk,

Samaneh Ghofrani

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 21, 2024

Abstract N ‐Sulfonyl‐1,2,3‐triazoles are valuable precursors for the generation of α‐imino carbene intermediates in presence metal catalysts, especially rhodium(II) complexes. Due to electrophilic and nucleophilic nitrogen, these reactive can easily be incorporated into many annulations, cycloadditions, C−H or O/N/S−H bond insertions functionalization reactions. A large number pharmaceutically important nitrogen‐based building blocks constructed via this direct atom‐economical strategy. In review, we have described transformations ‐sulfonyl‐1,2,3‐triazoles based on intermediates.

Язык: Английский

Процитировано

1