Catalysis Science & Technology, Journal Year: 2023, Volume and Issue: 13(24), P. 7136 - 7148
Published: Jan. 1, 2023
DFT calculations disclosed that the central functional group could induce a favorable chiral environment and determine enantioselectivity for Brønsted C–H acid catalysis.
Language: Английский
Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(21), P. 4393 - 4397
Published: Jan. 1, 2023
Herein, we describe a B(C 6 F 5 ) 3 -catalyzed redox-neutral β-functionalization of tertiary amines with cyclic-ketimines, achieving various 1,3-diamines containing the indolin-3-one moiety via borrowing hydrogen strategy.
Language: Английский
Citations
14
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(28), P. 18841 - 18847
Published: July 8, 2024
An asymmetric intramolecular spiro-amination to high steric hindering
Language: Английский
Citations
5
Advanced Science, Journal Year: 2024, Volume and Issue: 11(25)
Published: April 24, 2024
Abstract The efficient synthesis of chiral 2,2‐disubstituted indolin‐3‐ones is great importance due to its significant synthetic and biological applications. However, catalytic enantioselective methods for de novo such heterocycles remain scarce. Herein, a novel cyclizative rearrangement readily available anilines vicinal diketones the one‐step construction enantioenriched presented. reaction proceeds through self‐sorted [3+2] heteroannulation/regioselective dehydration/1,2‐ester shift process. Only phosphoric acid employed promote entire sequence simplify manipulation this protocol. Various common aniline derivatives are successfully applied asymmetric as 1,3‐binuclephiles first time. Remarkably, observed stereoselectivity proposed originate from an amine‐directed regio‐ ortho ‐Csp 2 ‐H addition ketones. A range transformations resulting products demonstrated well.
Language: Английский
Citations
4
Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 932 - 936
Published: Jan. 23, 2025
A chiral phosphoric acid-catalyzed efficient, operationally simple, general method for straightforward syntheses of axially arylpyrazole employing N-alkyl 3-aryl-5-aminopyrazoles reacting with azonaphthalenes was achieved. wide variety heterobiaryl diamines in generally good yields excellent enantioselectivities were obtained under mild conditions. In addition, a scaled-up experiment and postmodification the product further highlighted synthetic utility.
Language: Английский
Citations
0
Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
2,2-Disubstituted indolin-3-ones, which are essential components in many manufactured chemicals, dyes, and naturally occurring bioactive alkaloids, have emerged as exciting synthetic targets. Much attention has been paid to accessing these units, particularly an asymmetric fashion, during the last decade. In this review article, we discuss current state of available methods with existing mechanistic pathways for chiral indolin-3-one derivatives under various catalytic systems. This overall presentation protocols access 2,2-disubstituted or fused indolin-3-ones aza-quaternary centre is categorized based on reaction modes 2-substituted-3H-indole-3-one other similar protocols.
Language: Английский
Citations
0
Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 533 - 540
Published: March 10, 2025
A valuable vinylogous addition reaction between 4-alkylidene-5-aminopyrazoles and alkyl trifluoropyruvates leading to highly functionalized tertiary alcohols bearing a trifluoromethyl group pyrazole ring is presented. The corresponding are obtained in moderate good yields (up 80%) high diastereoselectivity 7:1).
Language: Английский
Citations
0
Organic Letters, Journal Year: 2024, Volume and Issue: 26(6), P. 1154 - 1159
Published: Feb. 7, 2024
The direct functionalization of β-C(sp2)-H bonds in enamides has garnered increasing attention within the realm organic synthesis. However, these remarkable advancements are predominantly dependent on transition metals; limited success been achieved via organocatalytic catalysis. Herein, we report a CPA-catalyzed cascade intramolecular cyclization to synthesize chiral dihydropyrimido[1,6-a]indoles bearing gem-difluoromethylene. Moreover, this methodology enables synthesis diverse with outstanding enantioselectivities moderate high yields.
Language: Английский
Citations
3
Beilstein Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 19, P. 956 - 981
Published: June 28, 2023
The aza-Friedel–Crafts reaction allows an efficient coupling of electron-rich aromatic systems with imines for the facile incorporation aminoalkyl groups into ring. This has a great scope forming aza-stereocenters which can be tuned by different asymmetric catalysts. review assembles recent advances in reactions mediated organocatalysts. mechanistic interpretation origin stereoselectivity is also explained.
Language: Английский
Citations
7
Chemical Communications, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
The catalytic asymmetric electrophilic functionalization of the less reactive N-heteroaromatic compounds has been reported using approach introduction an exocyclic amino substituent.
Language: Английский
Citations
2
Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(18)
Published: Aug. 2, 2023
Abstract A facile enantioselective alkynylation of cyclic ketimines attached to a neutral functional group utilizing the dual Cu(I)‐CPA catalysis is described. The strategy 2‐aryl‐3 H ‐indol‐3‐one directly chiral propargylic amines containing indolin‐3‐one moiety in good yields and enantioselectivities. Moreover, gram‐scale synthesis propargylamines based C2‐quaternary indolin‐3‐ones was performed. synthetic applications were confirmed by transformations products with no decrease yield enantioselectivity.
Language: Английский
Citations
4