Tetrahedron Chem, Journal Year: 2022, Volume and Issue: 1, P. 100007 - 100007
Published: Feb. 3, 2022
Language: Английский
Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(15), P. 12544 - 12747
Published: July 17, 2022
1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability stabilize ionic species, transfer protons, and engage range of other intermolecular interactions. The use this exponentially increased the past decade become choice some areas, such as C–H functionalization chemistry. In review, following brief history HFIP an overview physical properties, literature examples reactions using or additive are presented, emphasizing effect each reaction.
Language: Английский
Citations
325
Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(17)
Published: Jan. 26, 2022
Abstract The first highly atroposelective construction of N−N axially chiral indole scaffolds was established via a new strategy de novo ring formation. This makes use the organocatalytic asymmetric Paal–Knorr reaction well‐designed N ‐aminoindoles with 1,4‐diketones, thus affording ‐pyrrolylindoles in high yields and excellent atroposelectivities (up to 98 % yield, 96 ee). In addition, this is applicable for synthesis bispyrroles 97 More importantly, such heterocycles can be converted into organocatalysts applications catalysis, some molecules display potent anticancer activity. work not only provides but also offers members atropisomer family promising synthetic medicinal chemistry.
Language: Английский
Citations
140
Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 40(18), P. 2151 - 2160
Published: May 31, 2022
Comprehensive Summary A new strategy for the enantioselective synthesis of axially chiral 3,3'‐bisindoles was devised by direct coupling two indole rings. This makes use C3‐umpolung reactivity 2‐indolylmethanols, which enables catalytic asymmetric addition reaction 2‐indolylmethanols with rationally designed 2‐substituted indoles, thus constructing 3,3'‐bisindole scaffolds in overall excellent yields (up to 98%) high enantioselectivities 96 : 4 er). approach not only has overcome challenges five‐five‐membered heterobiaryls, but also represents a application catalysis. More importantly, this class can undergo variety post‐functionalizations give 3,3'‐bisindole‐based organocatalysts, have found their preliminary applications
Language: Английский
Citations
111
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(15)
Published: Feb. 7, 2023
This study establishes the first organocatalytic enantioselective synthesis of axially chiral N,N'-bisindoles via phosphoric acid-catalyzed formal (3+2) cycloadditions indole-based enaminones as novel platform molecules with 2,3-diketoesters, where de novo indole-ring formation is involved. Using this new strategy, various were synthesized in good yields and excellent enantioselectivities (up to 87 % yield 96 ee). More importantly, class exhibited some degree cytotoxicity toward cancer cells was derived into phosphine ligands high catalytic activity. provides a strategy for using asymmetric organocatalysis realize applications such scaffolds medicinal chemistry catalysis.
Language: Английский
Citations
91
Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(4), P. 966 - 992
Published: Feb. 15, 2023
Language: Английский
Citations
82
Nature Synthesis, Journal Year: 2022, Volume and Issue: 1(6), P. 426 - 438
Published: June 6, 2022
Language: Английский
Citations
76
Science China Chemistry, Journal Year: 2022, Volume and Issue: 65(10), P. 1929 - 1937
Published: Sept. 13, 2022
Language: Английский
Citations
76
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(37)
Published: June 24, 2023
Catalytic asymmetric construction of chiral indole-fused rings has become an important issue in the chemical community because significance such scaffolds. In this work, we have accomplished first catalytic (4+2) and (4+3) cycloadditions 2,3-indolyldimethanols by using indoles 2-naphthols as suitable reaction partners under catalysis phosphoric acids, constructing enantioenriched six-membered seven-membered high yields with excellent enantioselectivities. addition, approach is used to realize enantioselective challenging tetrahydroindolocarbazole scaffolds, which are found show promising anticancer activity. More importantly, theoretical calculations pathways activation mode offer in-depth understanding class indolylmethanols. This work not only settles challenges realizing indolyldimethanols but also provides a powerful strategy for rings.
Language: Английский
Citations
54
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(13)
Published: Jan. 30, 2024
Abstract Herein, we have synthesized multifunctionalized 2‐oxa‐3‐azabicyclo[3.1.1]heptanes, which are considered potential bioisosteres for meta ‐substituted arenes, through Eu(OTf) 3 ‐catalyzed formal dipolar [4π+2σ] cycloaddition of bicyclo[1.1.0]butanes with nitrones. This methodology represents the initial instance fabricating bicyclo[3.1.1]heptanes adorned multiple heteroatoms. The protocol exhibits both mild reaction conditions and a good tolerance various functional groups. Computational density theory calculations support that mechanism likely involves nucleophilic addition nitrones to bicyclo[1.1.0]butanes, succeeded by an intramolecular cyclization. synthetic utility this novel has been demonstrated in concise synthesis analogue Rupatadine.
Language: Английский
Citations
49
Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(8), P. 2629 - 2636
Published: June 26, 2024
Language: Английский
Citations
26