Pd/Cu-Cocatalyzed Asymmetric Cascade Heck/Tsuji–Trost Reaction to Access Non-natural Tryptophans DOI
Panpan Li, Yang Zhang,

Zijiao Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 20, 2024

A Pd-catalyzed asymmetric Heck cascade reaction involving the intramolecular carbopalladation of unsaturated hydrocarbons, followed by nucleophilic trapping resulting palladium species, is a powerful approach for constructing chiral N-heterocycles. However, use prochiral nucleophiles in these reactions remains significantly underexplored. Herein, we report novel Pd/Cu catalytic system Heck/Tsuji–Trost allenamides and aldimine esters. This robust method allows rapid synthesis wide range enantiopure non-natural α-substituted tryptophans high yields (up to 99% yield) with excellent enantioselectivities 98% ee). Additionally, synthetic utility this protocol demonstrated through scale-up experiments diverse valuable transformations.

Language: Английский

Recent Advancement in the Conversion of 1,2,3‐Benzotriazin‐4(3H)‐One to Other Heterocyclic Systems and Their Applications: A Concise Review DOI Open Access
Zunera Khalid, Hafiz Adnan Ahmad, Munawar Ali Munawar

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(5)

Published: Feb. 1, 2025

Abstract The nitrogen containing 1,2,3‐benzotriazin‐4(3 H )‐one is structurally worthwhile system for its notable applications in the synthesis of N─ , O ─ and S─ heterocycles bears pivotal significant usage pharmaceutical industrial chemicals. Today most common items like dyes, cosmetics, sanitizers, insecticides plastics are based on heterocyclic moieties. Different starting materials used industrially formation diverse but a valuable structure to prepare numerous products. These conversions radiation or metal‐catalyzed denitrogenation annulation type reactions provide easy, one‐step atom‐economical route. vast significance their cheap make this subject interesting scientific researchers industrialists. This mini review summarizes recent developments transformation ring various other structures phenanthridinones, isoquinolones, coumarin‐1‐imines, benzamides, pyrroloquinazolinones, indolin‐1‐ones, 1,2‐benzisoselenazol‐3(2 )‐ones benzofuranones. Some emerging drugs ebselen, losartan, irbesartan, luotonin A, deoxyvasicinone mackinazolinone have been successfully synthesized from differently substituted benzotriazinones.

Language: Английский

Citations

0
Research Progress on Transition Metal Catalyzed Hydrocarbonation Reactions of N-Allenamines DOI
Junwei Wang, Hao Xue,

Yingyu Qu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(1), P. 151 - 151

Published: Jan. 1, 2025

Language: Английский

Citations

0
Synthesis of Substituted 1,2-Dihydroisoquinolines by Palladium-Catalyzed Cascade Cyclization–Coupling of Trisubstituted Allenamides with Arylboronic Acids DOI Creative Commons
Masahiro Yoshida,

Ryunosuke Imaji,

Shinya Shiomi

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(12), P. 2917 - 2917

Published: June 19, 2024

1,2-Dihydroisoquinolines are important compounds due to their biological and medicinal activities, numerous approaches synthesis have been reported. Recently, we reported a facile of trisubstituted allenamides via N-acetylation followed by DBU-promoted isomerization, where various substituted were conveniently synthesized from readily available propargylamines with high efficiency. In light this research background, focused on the utility methodology for 1,2-dihydroisoquinolines. study, palladium-catalyzed cascade cyclization–coupling containing bromoaryl moiety arylboronic acids is described. When N-acetyl diphenyl-substituted allenamide phenylboronic acid treated 10 mol% Pd(OAc)2, 20 P(o-tolyl)3, 5 equivalents NaOH in dioxane/H2O (4/1) at 80 °C, reaction proceeded afford 1,2-dihydroisoquinoline. The intramolecular cyclization, transmetallation resulting allylpalladium intermediate. A variety highly 1,2-dihydroisoquinolines concisely obtained using because allenamides, as substrates, prepared one step.

Language: Английский

Citations

0
Pd/Cu-Cocatalyzed Asymmetric Cascade Heck/Tsuji–Trost Reaction to Access Non-natural Tryptophans DOI
Panpan Li, Yang Zhang,

Zijiao Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 20, 2024

A Pd-catalyzed asymmetric Heck cascade reaction involving the intramolecular carbopalladation of unsaturated hydrocarbons, followed by nucleophilic trapping resulting palladium species, is a powerful approach for constructing chiral N-heterocycles. However, use prochiral nucleophiles in these reactions remains significantly underexplored. Herein, we report novel Pd/Cu catalytic system Heck/Tsuji–Trost allenamides and aldimine esters. This robust method allows rapid synthesis wide range enantiopure non-natural α-substituted tryptophans high yields (up to 99% yield) with excellent enantioselectivities 98% ee). Additionally, synthetic utility this protocol demonstrated through scale-up experiments diverse valuable transformations.

Language: Английский

Citations

0