Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(7), P. 109322 - 109322
Published: Nov. 19, 2023
Language: Английский
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(14), P. 3662 - 3668
Published: Jan. 1, 2023
With the aid of chiral phosphoric acid, enantioselective 1,6-addition tryptamines to in situ formed alkynyl 7-methylene-7 H -indoles from tertiary α-(7-indolyl)methanols has been established, furnishing axially tetrasubstituted allenes high yields.
Language: Английский
Citations
16
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1078 - 1083
Published: Jan. 17, 2024
Abstract An organocatalytic remote stereocontrolled 1,8‐conjugated addition of in situ formed propargylic aza‐ p ‐QMs from α‐(4‐aminophenyl) alcohols and indole‐2‐carboxylates was developed, affording axially chiral tetrasubstituted allenes 62–99% yield with 52–99% ee. The synthetic strategy not only enriches the chemistry ‐quinone methides, but also provides an alternative tool for preparation allenes.
Language: Английский
Citations
4
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(12), P. 1926 - 1933
Published: May 17, 2023
Abstract Conjugate addition is one of the most powerful and practical methods for formation carbon‐carbon carbon‐heteroatom bonds in organic synthesis. Owing to rapid development asymmetric catalysis, significant progress has been made field conjugate addition, such as 1,4‐addition 1,6‐addition. However, formidable challenge controlling chemo‐, regio‐ stereoselectivity arises with extended conjugated systems. Recently, aid Brønsted acids functionalized benzyl alcohols indolylmethanols successfully developed suitable precursors electron‐deficient systems organocatalytic remote stereocontrolled additions. This review investigates advances enantioselective 1,8‐conjugate 1,10‐conjugate situ formed from alcohols, which organized according substrates.
Language: Английский
Citations
10
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 26, 2025
Organocatalytic enantioselective formal nucleophilic substitution reactions of α-(2-hydroxynaphthalen-8-yl)propargyl alcohols with 1-(1H-indol-3-yl)naphthalen-2-ols have been established for the first time. With aid a suitable chiral phosphoric acid, alkynyl 8-methylenenaphthalen-2(8H)-one was formed in situ from corresponding alcohol, followed by 1,6-conjugate additions to afford number enantioenriched (Ra,Sc)-2,3-disubstituted indoles 50-80% yields 81-93% ee and (Sa,Sc)-2,3-disubstituted 18-40% 79-96% ee. Notably, these products were characterized presence functional groups, including indole, naphthol, units, while exhibiting both axial central chirality.
Language: Английский
Citations
0
Chirality, Journal Year: 2022, Volume and Issue: 34(7), P. 1019 - 1034
Published: May 6, 2022
Abstract A readily available chiral cyclohexanediamine‐derived bifunctional tertiary amine‐squaramide catalyst is more effective for the asymmetric dearomative 1,3‐dipolar cycloaddition of 2‐nitrobenzofurans and N ‐2,2,2‐trifluoroethylisatin ketimines. range structurally diverse spiro‐fused polyheterocyclic compounds containing oxindole, pyrrolidine, hydrobenzofuran motifs were smoothly obtained in excellent results (up to 99% yield, >20:1 dr all cases up ee). This method features high efficiency, mild reaction conditions, exquisite induction, wide functional group tolerance, great potential scale‐up synthesis, attractive product diversification.
Language: Английский
Citations
15
Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(2), P. 252 - 272
Published: Dec. 5, 2022
Four organocatalytic approaches for the synthesis of axially chiral tetrasubstituted allenes are described with new critical insights into reaction scope and mechanisms.
Language: Английский
Citations
15
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown
Published: Oct. 17, 2024
Chiral tetrasubstituted allenes have emerged as important architectures for engineering biologically active compounds. The construction of unique allene scaffolds with precise control continuous central and axial chirality remains yet to be developed. Here, we report a remote enantioselective ϵ-alkylation yne-propargylic acetates enals enabled by NHC copper cooperative catalysis, leading series excellent enantioselectivities (up >99 % ee) diastereoselectivities >95 : 5 dr). This method features high regioselectivity simultaneous chirality. Mechanistic studies suggest activation mode synergistic distal created from the ethynylallenylidenes.
Language: Английский
Citations
2
Organic Letters, Journal Year: 2022, Volume and Issue: 24(43), P. 7955 - 7960
Published: Oct. 24, 2022
Supramolecular asymmetric catalysis has arisen from the in-depth intersection of supramolecular chemistry and due to its unique advantages in building chiral catalyst libraries regulating performance catalysts. Herein, we combine crown ether based host-guest with phosphoric acid mediated actualize regulation catalytic two-component tandem acetalization reactions. By comparison reaction without interaction, improvement up 72% yield increases 13% enantioselectivity were acquired after addition alkali metal guests, which demonstrated great this strategy.
Language: Английский
Citations
10
Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1297, P. 136919 - 136919
Published: Oct. 28, 2023
Language: Английский
Citations
6
ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(48)
Published: Dec. 21, 2023
Abstract The importance of indole‐based heterocycle scaffolds in medicinal chemistry has increased as a result their significant pharmacological and biological characteristics. These compounds′ the discovery creation cutting‐edge medications to treat variety diseases is an instance worth. current study highlights numerous methods available create different favourable medical uses with literature that been published up 2023.
Language: Английский
Citations
6