Protecting-group-free synthesis of hydroxyesters from amino alcohols

2020 ◽  
Vol 56 (74) ◽  
pp. 10938-10941
Author(s):  
Guillaume Reynard ◽  
Eve-Marline Joseph-Valcin ◽  
Hélène Lebel
Keyword(s):  
Carboxylic Acids ◽  
Continuous Flow ◽  
Amino Alcohols ◽  
Batch Processes ◽  
Protecting Group

The synthesis of hydroxyesters from carboxylic acids and unprotected amino alcohols in both continuous flow and batch processes is reported.

Room Temperature Flow Electrochemistry as a Means of Retaining the “Memory of Chirality” via Hofer Moest Type Reaction

2020 ◽  
Author(s):  
Tomas Hardwick ◽  
Rossana Cicala ◽  
Nisar Ahmed
Keyword(s):  
Continuous Flow ◽  
Room Temperature ◽  
Biological Activities ◽  
Supporting Electrolyte ◽  
Enantiomeric Excess ◽  
Flow Chemistry ◽  
Batch Processes ◽  
Enabling Technology ◽  
Chiral Compounds ◽  
Memory Of Chirality

<p>Many chiral compounds have become of great interest to the pharmaceutical industry as they possess various biological activities. Concurrently, the concept of “memory of chirality” has been proven as a powerful tool in asymmetric synthesis, while flow chemistry has begun its rise as a new enabling technology to add to the ever increasing arsenal of techniques available to the modern day chemist. Here, we have employed a new simple electrochemical microreactor design to oxidise an L-proline derivative at room temperature in continuous flow. Flow performed in microreactors offers up a number of benefits allowing reactions to be performed in a more convenient and safer manner, and even allow electrochemical reactions to take place without a supporting electrolyte due to a very short interelectrode distance. By the comparison of electrochemical oxidations in batch and flow we have found that continuous flow is able to outperform its batch counterpart, producing a good yield (71%) and a better enantiomeric excess (64%) than batch with a 98% conversion. We have, therefore, provided evidence that continuous flow chemistry has the potential to act as a new enabling technology to replace some aspects of conventional batch processes. </p>

scholarly journals Continuous Flow Photochemical and Thermal Multi-Step Synthesis of Bioactive 3-Arylmethylene-2,3-Dihydro-1H-Isoindolin-1-Ones

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4527 ◽  
Author(s):  
Saira Mumtaz ◽  
Mark J. Robertson ◽  
Michael Oelgemöller
Keyword(s):  
Local Anesthetic ◽  
Continuous Flow ◽  
Reaction Times ◽  
Batch Processes ◽  
Thermal Flow

An effective multi-step continuous flow approach towards N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones, including the local anesthetic compound AL-12, has been realized. Compared to the traditional decoupled batch processes, the combined photochemical–thermal–thermal flow setup rapidly provides the desired target compounds in superior yields and significantly shorter reaction times.

Dimethyl carbonate as a non-innocent benign solvent for the multistep continuous flow synthesis of amino alcohols

2018 ◽  
Vol 3 (4) ◽  
pp. 572-578 ◽  
Author(s):  
Raul Porcar ◽  
Pedro Lozano ◽  
Maria Isabel Burguete ◽  
Eduardo Garcia-Verdugo ◽  
Santiago V. Luis
Keyword(s):  
Environmental Impact ◽  
Continuous Flow ◽  
Dimethyl Carbonate ◽  
Amino Alcohols ◽  
Flow Synthesis

An efficient methodology for the production and resolution of amino alcohols with a low environmental impact has been developed.

Chiroptical sensing of unprotected amino acids, hydroxy acids, amino alcohols, amines and carboxylic acids with metal salts

2019 ◽  
Vol 55 (44) ◽  
pp. 6297-6300 ◽  
Author(s):  
Ciarán C. Lynch ◽  
Zeus A. De los Santos ◽  
Christian Wolf
Keyword(s):  
Amino Acids ◽  
Carboxylic Acids ◽  
Amino Alcohols ◽  
Metal Salts ◽  
Hydroxy Acids ◽  
Optical Chirality ◽  
Iron Palladium

Optical chirality sensing of unprotected amino acids, hydroxy acids, amino alcohols, amines and carboxylic acids based on a practical mix-and-measure protocol with readily available copper, iron, palladium, manganese, cerium or rhodium salts is demonstrated.

Synthesis of novel chiral fluorescent sensors and their application in enantioselective discrimination of chiral carboxylic acids

2019 ◽  
Vol 43 (9-10) ◽  
pp. 340-346 ◽  
Author(s):  
Qiuhan Yu ◽  
Weiwen Lu ◽  
Zhiqiang Ding ◽  
Min Wei ◽  
Zhenya Dai
Keyword(s):  
Carboxylic Acids ◽  
Chiral Recognition ◽  
Amino Alcohols ◽  
Fluorescent Sensors ◽  
Enantiomerically Pure ◽  
Wide Range

Novel chiral fluorescent sensors are synthesized from a dibromide containing a tetraphenylethylene moiety and enantiomerically pure amino alcohols and an amine. The sensors are applied for the chiral recognition of a wide range of chiral carboxylic acids and related derivatives.

Synthesis of photolabile protecting group (PPG) protected uronic acid building blocks: applications in carbohydrate synthesis with the assistance of a continuous flow photoreactor

2019 ◽  
Vol 6 (23) ◽  
pp. 3859-3863 ◽  
Author(s):  
Varsha Tiwari ◽  
Adesh Kumar Singh ◽  
Priyanka Chaudhary ◽  
Peter H. Seeberger ◽  
Jeyakumar Kandasamy
Keyword(s):  
Continuous Flow ◽  
Uronic Acid ◽  
Building Blocks ◽  
Protecting Group ◽  
Carbohydrate Synthesis ◽  
Photolabile Protecting Group

Photolabile groups protected uronic acid building blocks were synthesized and used for carbohydrate synthesis with the help of a continuous flow photo-reactor.

ChemInform Abstract: 1,2,3,4-Tetrahydro-1-naphthyl Ester as a Selective Protecting Group for Carboxylic Acids.

ChemInform ◽  
2010 ◽  
Vol 30 (44) ◽  
pp. no-no
Author(s):  
Christopher J. Slade ◽  
Carol A. Pringle ◽  
Ian G. Sumner
Keyword(s):  
Carboxylic Acids ◽  
Protecting Group
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