2020
DOI: 10.1039/d0cc01403f
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Micro-flow synthesis of β-amino acid derivatives via a rapid dual activation approach

Abstract: Rapid dual activation (≤3.3 s) of both β-amino acid N-carboxy anhydride and alkyl chloroformate for the synthesis of a β-amino acid-derived scaffold was demonstrated.

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Cited by 13 publications
(6 citation statements)
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“…Frontiers in Chemical Engineering frontiersin.org the advantage of the flow microreactors, highly-selective chemical reactions have been achieved (Ashikari et al, 2019;Sugisawa et al, 2020;Ashikari et al, 2021). Based on this idea, we envisaged that aryl lithiums bearing electrophilic functionalities are generated by functional-group-tolerant halogen-lithium exchange reactions and, before they decompose, are converted to aryl zincs.…”
Section: Methodsmentioning
confidence: 99%
“…Frontiers in Chemical Engineering frontiersin.org the advantage of the flow microreactors, highly-selective chemical reactions have been achieved (Ashikari et al, 2019;Sugisawa et al, 2020;Ashikari et al, 2021). Based on this idea, we envisaged that aryl lithiums bearing electrophilic functionalities are generated by functional-group-tolerant halogen-lithium exchange reactions and, before they decompose, are converted to aryl zincs.…”
Section: Methodsmentioning
confidence: 99%
“…Trichloroacetic anhydride was selected as the acetylation agent because it generated soluble salts (tributylammonium trichloroacetate) with TBA. The syntheses of β-amino acid derivatives have been demonstrated using rapid dual activation (<3.3 s) of both β-amino acid N-carboxy anhydride and alkyl chloroformate under micro-flow conditions [48]. A single-step micro-flow synthesis of amino acid N-carboxy anhydride was previously reported [49,50].…”
Section: Organocatalyzed Decarboxylative Trichloromethylation Of Morita-baylis-hillman Adductsmentioning
confidence: 99%
“…Additionally, a flow reactor has a high surface area to volume ratio, shorter diffusion pathways and excellent heat and mass transfer, which can lead to a shorter reaction time and a higher yield. [14][15][16][17][18][19][20][21][22][23][24][25][26] The use of flow systems in Stille polycondensation of conjugated polymers has been shown to improve the reproducibility of the process, leading to higher-quality products and better device performance. [27][28][29][30][31] Additionally, recent studies have focused on identifying key factors that affect molecular weight in the synthesis of conjugated polymers in flow.…”
Section: Introductionmentioning
confidence: 99%