{"id":4446,"date":"2023-02-14T13:30:35","date_gmt":"2023-02-14T12:30:35","guid":{"rendered":"https:\/\/www.tarosdiscovery.com\/unkategorisiert\/continuous-flow-systems-for-the-enantioselective-phase-transfer-catalytic-synthesis-of-quaternary-amino-acids\/"},"modified":"2024-01-26T09:57:49","modified_gmt":"2024-01-26T08:57:49","slug":"continuous-flow-systems-for-the-enantioselective-phase-transfer-catalytic-synthesis-of-quaternary-amino-acids","status":"publish","type":"post","link":"https:\/\/www.tarosdiscovery.com\/de\/news\/continuous-flow-systems-for-the-enantioselective-phase-transfer-catalytic-synthesis-of-quaternary-amino-acids\/","title":{"rendered":"Continuous Flow Systems for the Enantioselective Phase Transfer Catalytic Synthesis of Quaternary Amino Acids"},"content":{"rendered":"\t\t
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Laboratory Scale Continuous Flow Systems for the Enantioselective Phase Transfer Catalytic Synthesis of Quaternary Amino Acids<\/h1>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/section>\n\t\t\t\t
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Milena Krsti\u0107, Sergio Rossi, Miguel Sanz, Alessandra Puglisi<\/p>\n

Molecules 2023, 28(3), 1002;\u00a0https:\/\/doi.org\/10.3390\/molecules28031002<\/a><\/p>\n\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Abstract:<\/strong><\/p>\n

The use of stereoselective phase-transfer catalysis as a reliable method for the enantioselective synthesis of optically active \u03b1-amino acid derivatives using achiral Schiff base esters has been well-developed in batch in the last 40 years. Recently, continuous flow technology has become of great interest in the academy and industry, since it offers safer process operating conditions and higher efficiency compared to a traditional batch processing. Herein, we wish to report the first example of enantioselective phase transfer benzylation of alanine Schiff base ester, under continuous flow conditions. Two different methodologies were investigated: a liquid-solid phase transfer catalytic benzylation using a packed-bed reactor and a liquid-liquid phase transfer catalytic benzylation in continuous stirred-tank reactors. Liquid-liquid phase transfer process in flow showed slightly better productivity than the batch process, while solid-liquid phase transfer benzylation proved much more advantageous in terms of productivity and space-time yield. Furthermore, continuous flow system allowed the isolation of benzylated product without any work up, with a significant simplification of the process. In both cases, phase transfer asymmetric benzylation promoted by Maruoka catalyst demonstrated high enantioselectivity of target quaternary amino ester in flow, up to 93% ee.<\/p>\n\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t

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Interessiert Sie diese Publikation? Kontaktieren Sie unsere Wissenschaftler<\/h2>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Medizinalchemie<\/p>\n\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Wirkstoffforschung<\/h3>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Das internationale Team von Taros verf\u00fcgt kombiniert \u00fcber mehr als 180 Jahre Erfahrung in der pharmazeutischen F&E. Als Team haben wir an mehr als 120 biomolekularen\u2026<\/p>\n\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Performance Chemicals<\/p>\n\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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Auftragssynthese<\/h3>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Unsere Kunden profitieren von der Synthese erster kg-Mengen innovativer Fein- und Spezialchemikalien, Effizienzsteigerung und Kostensenkung von\u2026<\/p>\n

<\/div>\n<\/div>\n<\/div>\n\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Interessiert?<\/h3>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Als ein europaweit f\u00fchrendes und unabh\u00e4ngiges Auftragsforschungsunternehmen (CRO) bieten wir Ihnen das gesamte Spektrum der (metall)organischen Synthesechemie.<\/h3>\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t
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Wir praktizieren einen pragmatischen sowie kundenorientierten Ansatz, um die Erwartungen an uns trotz h\u00f6chster Herausforderungen zu \u00fcbertreffen. Unsere erfahrenen Chemiker sind geschult, wirtschaftliche, \u00f6kologische sowie sicherheitstechnische Bedingungen f\u00fcr alle Phasen des Projekts zu evaluieren.<\/p>\n\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t

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\n\t\t\t\t\t\n\t\t\t\t\t\t\n\t\t\t\t\t\t\t\t\tKontakt<\/span>\n\t\t\t\t\t<\/span>\n\t\t\t\t\t<\/a>\n\t\t\t\t<\/div>\n\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/section>\n\t\t\t\t\t<\/div>\n\t\t<\/div>\n\t\t\t\t\t<\/div>\n\t\t<\/section>\n\t\t\t\t<\/div>\n\t\t","protected":false},"excerpt":{"rendered":"

Die Nutzung der stereoselektiven Phasentransferkatalyse als zuverl\u00e4ssige Methode zur enantioselektiven Synthese optisch aktiver \u03b1-Aminos\u00e4urederivate…<\/p>\n","protected":false},"author":5,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"default","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"default","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"var(--ast-global-color-4)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"footnotes":""},"categories":[23],"tags":[],"class_list":["post-4446","post","type-post","status-publish","format-standard","hentry","category-publikationen"],"_links":{"self":[{"href":"https:\/\/www.tarosdiscovery.com\/de\/wp-json\/wp\/v2\/posts\/4446","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.tarosdiscovery.com\/de\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.tarosdiscovery.com\/de\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.tarosdiscovery.com\/de\/wp-json\/wp\/v2\/users\/5"}],"replies":[{"embeddable":true,"href":"https:\/\/www.tarosdiscovery.com\/de\/wp-json\/wp\/v2\/comments?post=4446"}],"version-history":[{"count":1,"href":"https:\/\/www.tarosdiscovery.com\/de\/wp-json\/wp\/v2\/posts\/4446\/revisions"}],"predecessor-version":[{"id":6344,"href":"https:\/\/www.tarosdiscovery.com\/de\/wp-json\/wp\/v2\/posts\/4446\/revisions\/6344"}],"wp:attachment":[{"href":"https:\/\/www.tarosdiscovery.com\/de\/wp-json\/wp\/v2\/media?parent=4446"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.tarosdiscovery.com\/de\/wp-json\/wp\/v2\/categories?post=4446"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.tarosdiscovery.com\/de\/wp-json\/wp\/v2\/tags?post=4446"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}