19438-10-9Relevant articles and documents
Syntheses of (6S)-6-fluoro- and (6R)-6-hydroxyshikimic acids
Song, Chuanjun,Jiang, Shende,Singh, Gurdial
, p. 9069 - 9071 (2001)
(6S)-6-Fluoroshikimic acid 2 and (6R)-6-hydroxyshikimic acid 3 have been synthesised via an OsO4-catalysed dihydroxylation of diene 6, which was derived from (-)-shikimic acid 1.
A scalable and safe continuous flow procedure for in-line generation of diazomethane and its precursor MNU
Lehmann
, p. 1449 - 1453 (2017)
Diazomethane is a valuable C1-building block for organic synthesis. Due to its intrinsic reactivity and instability, handling of this reagent is associated with serious safety hazards. Herein we present a simple and robust continuous flow process, allowing a safe and on-demand generation of diazomethane with a productivity of 95-117 mmol h-1. The developed two-step process starts from non-hazardous N-methylurea, and generates and consumes N-methyl-N-nitrosourea (MNU) and diazomethane, thus enabling a safe and convenient scale-up to a multi-gram scale in a conventional synthesis laboratory.
Dioxetane formation and chemiluminescent emission upon the combination of a vinylphenol derivative with naphthalene endoperoxide
Umehara, Yui,Son, Aoi,Kondo, Teruyuki,Tanabe, Kazuhito
, p. 9472 - 9475 (2017)
We designed a chemiluminescent system using nanoparticles. We prepared mesoporous nanoparticles bearing naphthalene endoperoxide as a singlet oxygen generator in the pore and vinyl phenol derivative as an emission unit. The combination of these functional molecules gave highly efficient and bright chemiluminescence through the formation of a 1,2-dioxetane intermediate.
Carboxyl Methyltransferase Catalysed Formation of Mono- and Dimethyl Esters under Aqueous Conditions: Application in Cascade Biocatalysis
Ashbrook, Chloe,Carnell, Andrew J.,Goulding, Ellie,Hatton, Harry,Johnson, James R.,Kershaw, Neil M.,McCue, Hannah V.,Rigden, Daniel J.,Ward, Lucy C.
supporting information, (2022/02/21)
Carboxyl methyltransferase (CMT) enzymes catalyse the biomethylation of carboxylic acids under aqueous conditions and have potential for use in synthetic enzyme cascades. Herein we report that the enzyme FtpM from Aspergillus fumigatus can methylate a broad range of aromatic mono- and dicarboxylic acids in good to excellent conversions. The enzyme shows high regioselectivity on its natural substrate fumaryl-l-tyrosine, trans, trans-muconic acid and a number of the dicarboxylic acids tested. Dicarboxylic acids are generally better substrates than monocarboxylic acids, although some substituents are able to compensate for the absence of a second acid group. For dicarboxylic acids, the second methylation shows strong pH dependency with an optimum at pH 5.5–6. Potential for application in industrial biotechnology was demonstrated in a cascade for the production of a bioplastics precursor (FDME) from bioderived 5-hydroxymethylfurfural (HMF).
Rhodium-Catalyzed Twofold Unsymmetrical C-H Alkenylation-Annulation/Thiolation Reaction to Access Thiobenzofurans
Lin, Jian,Hu, Liuyu,Chen, Chao,Feng, Huijin,Yu, Yang,Yang, Yaxi,Zhou, Bing
supporting information, p. 1194 - 1198 (2021/02/20)
A Rh(III)-catalyzed twofold unsymmetrical C-H alkenylation-annulation/thiolation reaction has been developed, enabling the straightforward and efficient synthesis of various thiobenzofurans in one step. This robust protocol proceeds with a broad substrate scope and good functional group tolerance under relatively mild reaction conditions.
