Modular Synthesis of α‐Quaternary Chiral β‐Lactams via Three‐Component Asymmetric Kinugasa/Aldol or Kinugasa/Mannich Cascade Reactions DOI Open Access

Linxuan Wang,

Jialin Qi, Haoyu Li

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 7, 2024

The β-lactam scaffolds are the prevalent structural units in antibiotics and natural products. Herein, three-component asymmetric Kinugasa/aldol Kinugasa/Mannich cascade reactions have been developed for constructing α-quaternary chiral β-lactams. This method involved tandem reaction of alkynes, nitrones aldehydes (or imines), resulting formation three sequential stereocenters controlled by copper(I) catalysts bis(oxazolidine) ligands. protocol features high enantioselectivity, good efficiency, mild operational conditions, representing a practical sustainable synthetic tool construction functionalized

Язык: Английский

Identification of three unexpected new psychoactive substances at an Australian drug checking service DOI Creative Commons
Jess L. Algar, Douglas J. Lawes, Adam J. Carroll

и другие.

Drug Testing and Analysis, Год журнала: 2024, Номер 16(10), С. 1144 - 1154

Опубликована: Янв. 11, 2024

Abstract Drug checking is a harm reduction measure that provides people with the opportunity to confirm identity and purity of substances before consumption. The CanTEST Health Checking Service Australia's first fixed‐site drug service, where clients can learn about contents samples they provide while receiving tailored health advice. Three were recently presented service expectation 4‐fluoromethylphenidate (4F‐MPH) 1 , methoxetamine (MXE) 2 3‐methylmethcathinone (3‐MMC) 3 . all three did not meet these expectations remained unknown on‐site, as no high confidence identifications obtained. However, further analysis by nuclear magnetic resonance spectroscopy, resolution gas chromatography‐electron ionisation‐mass spectrometry liquid chromatography‐electrospray at nearby Australian National University allowed for structure elucidation 4‐fluoro‐α‐pyrrolidinoisohexanophenone (4F‐α‐PiHP) 4 1‐(4‐fluorobenzyl)‐4‐methylpiperazine (4F‐MBZP) 5 N ‐propyl‐1,2‐diphenylethylamine (propylphenidine) 6 respectively. Given expected have yet been described new psychoactive in literature, this study presents full characterisation each compound. As exemplified rapid identification unexpected substances, be used an effective method monitor unregulated market.

Язык: Английский

Процитировано

7

Deoxygenative photochemical alkylation of secondary amides enables a streamlined synthesis of substituted amines DOI Creative Commons
Antonio Pulcinella, Stefano Bonciolini, Robin Stuhr

и другие.

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Янв. 22, 2025

Abstract Secondary amines are vital functional groups in pharmaceuticals, agrochemicals, and natural products, necessitating efficient synthetic methods. Traditional approaches, including N -monoalkylation reductive amination, suffer from limitations such as poor chemoselectivity complexity. Herein, we present a streamlined deoxygenative photochemical alkylation of secondary amides, enabling the synthesis α-branched amines. Our method leverages triflic anhydride-mediated semi-reduction amides to imines, followed by radical step. This approach broadens utility facilitating late-stage modifications drug-like molecules saturated -substituted heterocycles. The pivotal role flow technology developing scalable robust process underscores practicality this method, significantly expanding organic chemist’s toolbox for complex amine synthesis.

Язык: Английский

Процитировано

0

Modular Synthesis of α‐Quaternary Chiral β‐Lactams via Three‐Component Asymmetric Kinugasa/Aldol or Kinugasa/Mannich Cascade Reactions DOI Open Access

Linxuan Wang,

Jialin Qi, Haoyu Li

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 7, 2024

The β-lactam scaffolds are the prevalent structural units in antibiotics and natural products. Herein, three-component asymmetric Kinugasa/aldol Kinugasa/Mannich cascade reactions have been developed for constructing α-quaternary chiral β-lactams. This method involved tandem reaction of alkynes, nitrones aldehydes (or imines), resulting formation three sequential stereocenters controlled by copper(I) catalysts bis(oxazolidine) ligands. protocol features high enantioselectivity, good efficiency, mild operational conditions, representing a practical sustainable synthetic tool construction functionalized

Язык: Английский

Процитировано

1