Article
Chemistry, Applied
Ruiwen Hu, Anjie Gong, Langxing Liao, Yan-Xin Zheng, Xin Liu, Peng Wu, Fushuai Li, Huili Yu, Jing Zhao, Long-Wu Ye, Binju Wang, Aitao Li
Summary: A general biocatalytic process has been achieved for efficient one-pot preparation of enantiopure beta-amino alcohols through asymmetric epoxidation of alkene substrates followed by aminolysis of epoxide intermediates. Hybrid cluster-continuum (HCC) model calculations reveal the mechanism and the role of water in mediating the aminolysis reaction. The chirality of the amino alcohol is determined by the absolute configuration of the epoxide formed in the enzymatic reaction.
CHINESE JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Physical
Andrew W. J. Platten, Andryj M. Borys, Eva Hevia
Summary: In this study, the use of potassium magnesiate complex as a catalyst for the hydrophosphinylation of styrenes was reported. The bimetallic approach showed higher catalytic activity and selectivity compared to single-metal components. Stoichiometric studies helped to determine the constitution of the active catalytic species and understand the influence of donors on catalytic activity. Mechanistic investigations suggested that the olefinic substrate insertion is the rate determining step.
Article
Chemistry, Multidisciplinary
Yi-Min Jiang, Yi Yu, Shao-Fen Wu, Hong Yan, Yaofeng Yuan, Ke-Yin Ye
Summary: An environmentally friendly and efficient electrochemical method has been developed for the synthesis of beta-fluorosulfones from styrenes using sulfonylhydrazides and triethylamine trihydrofluoride. The reaction conditions are mild and have a broad substrate scope, easily scalable to gram-scale preparation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Zenghui Ye, Rongjin Zhu, Feng Wang, Haobin Jiang, Fengzhi Zhang
Summary: Atom- and step-economic oxo-azidation and oxo-hydroxyphthalimidation of styrenes were developed under mild electrolytic conditions, leading to efficient synthesis of valuable alpha-azido or hydroxyphthalimide aromatic ketones from readily available starting materials. Mechanism studies revealed two different pathways involved in these transformations.
Article
Chemistry, Multidisciplinary
Xiaozhou Huang, Ya-Qing Hu, Cen Zhou, Ying Zheng, Xiao Zhang
Summary: The use of urushiol derivatives as catalysts derived from renewable and sustainable resources for the visible-light-induced decarboxylative coupling of amino acids with aldehydes is demonstrated. 1,2-amino alcohols are accessed in a transition-metal-free manner under environmentally friendly and redox-neutral conditions. Additionally, the application of an urushiol-derived film in visible-light photoredox catalysis is disclosed.
Article
Chemistry, Applied
Balaji Sundara Sekar, Jiwei Mao, Benedict Ryan Lukito, Zilong Wang, Zhi Li
Summary: Enzyme cascades were developed to convert styrene into enantiopure (R)- and (S)-2-phenylglycinols, as well as other substituted styrenes and indene into substituted phenylglycinols and 1-amino-2-indanol with high enantioselectivity. Enantioselective enzyme cascades were also developed to produce (R)- and (S)-2-phenylglycinols from bio-based L-phenylalanine. Combining L-phenylalanine biosynthesis pathway with enantioselective cascade in one strain or coupled strains enabled the synthesis of (R)- and (S)-2-phenylglycinols from renewable feedstocks, enhancing production from glucose and glycerol.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Lauren N. Mendelsohn, Connor S. MacNeil, Madison R. Esposito, Tyler P. Pabst, David K. Leahy, Ian W. Davies, Paul J. Chirik
Summary: The cobalt-catalyzed asymmetric hydrogenation of indazole-containing enamides relevant to the synthesis of Zavegepant, a CGRP receptor antagonist, which is approved for the treatment of migraines, is described. Both neutral and cationic bis(phosphine)cobalt complexes were efficient precatalysts, providing excellent yield and enantioselectivities for related substrates, with key reactivity differences observed. The hydrogenation of the indazole-containing enamide was successfully scaled up to 20 g.
Article
Chemistry, Multidisciplinary
Daqi Lv, Qiao Sun, Huan Zhou, Liang Ge, Yanjie Qu, Taian Li, Xiaoxu Ma, Yajun Li, Hongli Bao
Summary: This study reports the iron-catalyzed intermolecular asymmetric aminoazidation and diazidation of styrenes, providing a direct and efficient pathway for constructing chiral nitrogen-containing compounds. The method shows potential value in the synthesis of chiral organoazides, with relatively low loading of catalyst and chiral ligand required for practical application.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Kaixue Xie, Martin Oestreich
Summary: Readily available cyclohexa-2,5-dien-1-ylcarbonyl chloride derivatives were used as stable HCl surrogates for transfer hydrochlorination of alkenes and alkynes. B(C6F5)(3) facilitated the stepwise fragmentation of acyl chlorides, allowing the addition of HCl across C-C double and triple bonds with Markovnikov selectivity at room temperature.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Toryn Dalton, Steffen Gressies, Mowpriya Das, Maximilian Niehues, Malte L. Schrader, Christian Gutheil, Bart Jan Ravoo, Frank Glorius
Summary: The research presents a mild and general catalytic system for the selective hydroheteroarylation of multiply substituted styrenes and heteroaromatic styrenes. The discovery of commercially available 2,2':5',2''-terthiophene as a key reagent opens up potential significant applications in organic synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Christopher J. J. Hall, William R. F. Goundry, Timothy J. Donohoe
Summary: Enantiopure 1,2-amino alcohols derived from abundant amino acids were used in C-C bond-forming hydrogen-borrowing alkylation reactions for the first time. The use of Ph*COMe aryl ketone facilitated the reactions, preventing racemisation of the amine stereocentre. The Ph* and trityl groups could be easily cleaved in one pot to give GABA products without further purification, allowing the two steps to be performed in sequence without isolation of the hydrogen-borrowing intermediate, eliminating the need for column chromatography.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Fang Wang, Jian Qin, Shengqing Zhu, Lingling Chu
Summary: An efficient metal-free protocol for the three-component sulfonylative pyridylation of styrenes via organic-photoredox catalysis has been described. This process enables the direct and selective installation of sulfonyl and heteroaryl motifs, tolerating a wide range of functional groups and complex molecular scaffolds. It could complement previous methods and be of interest in pharmaceutical research.
Review
Chemistry, Multidisciplinary
Andrey N. Pravdivtsev, Gerd Buntkowsky, Simon B. Duckett, Igor V. Koptyug, Jan-Bernd Hoevener
Summary: Nuclear magnetic resonance (NMR) is widely used in biochemical and biomedical research, with hyperpolarization expanding its applications. Parahydrogen (pH(2)) offers a fast and cost-efficient way for hyperpolarization, leading to a growing interest in hyperpolarized molecules like amino acids.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Daniel Sowa Prendes, Florian Papp, Nagesh Sankaran, Nardana Sivendran, Frederike Beyer, Christian Merten, Lukas J. Goossen
Summary: Arylglycines, which are important pharmacophores in several top-selling drugs, can now be synthesized from abundant aryl chlorides using a Pd-catalyzed Schollkopf-type amino acid synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
P. Rani, N. Pundir, Heena, A. Husain, A. K. K. Bhasin, K. K. Bhasin, G. Kumar
Summary: Two new doubly interpenetrated MOFs were studied and found to be effective in amino acid sensing and catalytic reactions.
MATERIALS TODAY CHEMISTRY
(2023)
