Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines

1,2,3,4-Tetrahydroisoquinolines form a valuable scaffold for a variety of bioactive secondary metabolites and commercial pharmaceuticals. Due to the harsh or complex conditions of the conventional chemical synthesis of this molecular motif, alternative mild reaction pathways are in demand. Here we p...

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Autores principales:	Andreas Sebastian Klein, Anna Christina Albrecht, Jörg Pietruszka
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	laccase TEMPO chemoenzymatic cascade pharmaceutical scaffold heterogeneous catalysis homogeneous catalysis Chemical technology TP1-1185 Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/a1066c6a63b84c6aab67d10621853eaa
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spelling	oai:doaj.org-article:a1066c6a63b84c6aab67d10621853eaa2021-11-25T17:06:41ZChemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines10.3390/catal111113892073-4344https://doaj.org/article/a1066c6a63b84c6aab67d10621853eaa2021-11-01T00:00:00Zhttps://www.mdpi.com/2073-4344/11/11/1389https://doaj.org/toc/2073-43441,2,3,4-Tetrahydroisoquinolines form a valuable scaffold for a variety of bioactive secondary metabolites and commercial pharmaceuticals. Due to the harsh or complex conditions of the conventional chemical synthesis of this molecular motif, alternative mild reaction pathways are in demand. Here we present an easy-to-operate chemoenzymatic one-pot process for the synthesis of tetrahydroisoquinolines starting from benzylic alcohols and an amino alcohol. We initially demonstrate the oxidation of 12 benzylic alcohols by a laccase/TEMPO system to the corresponding aldehydes, which are subsequently integrated in a phosphate salt mediated <i>Pictet–Spengler</i> reaction with <i>m</i>-tyramine. The reaction conditions of both individual reactions were analyzed separately, adapted to each other, and a straightforward one-pot process was developed. This enables the production of 12 1,2,3,4-tetrahydroisoquinolines with yields of up to 87% with constant reaction conditions in phosphate buffer and common laboratory glass bottles without the supplementation of any additives.Andreas Sebastian KleinAnna Christina AlbrechtJörg PietruszkaMDPI AGarticlelaccaseTEMPOchemoenzymatic cascadepharmaceutical scaffoldheterogeneous catalysishomogeneous catalysisChemical technologyTP1-1185ChemistryQD1-999ENCatalysts, Vol 11, Iss 1389, p 1389 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	laccase TEMPO chemoenzymatic cascade pharmaceutical scaffold heterogeneous catalysis homogeneous catalysis Chemical technology TP1-1185 Chemistry QD1-999
spellingShingle	laccase TEMPO chemoenzymatic cascade pharmaceutical scaffold heterogeneous catalysis homogeneous catalysis Chemical technology TP1-1185 Chemistry QD1-999 Andreas Sebastian Klein Anna Christina Albrecht Jörg Pietruszka Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines
description	1,2,3,4-Tetrahydroisoquinolines form a valuable scaffold for a variety of bioactive secondary metabolites and commercial pharmaceuticals. Due to the harsh or complex conditions of the conventional chemical synthesis of this molecular motif, alternative mild reaction pathways are in demand. Here we present an easy-to-operate chemoenzymatic one-pot process for the synthesis of tetrahydroisoquinolines starting from benzylic alcohols and an amino alcohol. We initially demonstrate the oxidation of 12 benzylic alcohols by a laccase/TEMPO system to the corresponding aldehydes, which are subsequently integrated in a phosphate salt mediated <i>Pictet–Spengler</i> reaction with <i>m</i>-tyramine. The reaction conditions of both individual reactions were analyzed separately, adapted to each other, and a straightforward one-pot process was developed. This enables the production of 12 1,2,3,4-tetrahydroisoquinolines with yields of up to 87% with constant reaction conditions in phosphate buffer and common laboratory glass bottles without the supplementation of any additives.
format	article
author	Andreas Sebastian Klein Anna Christina Albrecht Jörg Pietruszka
author_facet	Andreas Sebastian Klein Anna Christina Albrecht Jörg Pietruszka
author_sort	Andreas Sebastian Klein
title	Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines
title_short	Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines
title_full	Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines
title_fullStr	Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines
title_full_unstemmed	Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines
title_sort	chemoenzymatic one-pot process for the synthesis of tetrahydroisoquinolines
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/a1066c6a63b84c6aab67d10621853eaa
work_keys_str_mv	AT andreassebastianklein chemoenzymaticonepotprocessforthesynthesisoftetrahydroisoquinolines AT annachristinaalbrecht chemoenzymaticonepotprocessforthesynthesisoftetrahydroisoquinolines AT jorgpietruszka chemoenzymaticonepotprocessforthesynthesisoftetrahydroisoquinolines
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Chemoenzymatic One-Pot Process for the Synthesis of Tetrahydroisoquinolines

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