Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction

A chiral bio-based building block, prepared by the lipase-mediated desymmetrization of an erythritol derivative, was further functionalized and then submitted to stereoselective Passerini reactions, allowing the synthesis of a small library of new molecules. Thanks to the presence of different funct...

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Main Authors:	Gabriella Vitali Forconesi, Luca Banfi, Andrea Basso, Chiara Lambruschini, Lisa Moni, Renata Riva
Format:	Article
Language:	English
Published:	MDPI AG 2020-07-01
Series:	Molecules
Subjects:	multicomponent reactions Passerini reaction diastereoselective reactions lipase desymmetrization Michael reaction
Online Access:	https://www.mdpi.com/1420-3049/25/14/3227

id	doaj-9d1860a89f48419d9139a74738a93a50
record_format	Article
spelling	doaj-9d1860a89f48419d9139a74738a93a502020-11-25T03:07:30ZengMDPI AGMolecules1420-30492020-07-01253227322710.3390/molecules25143227Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini ReactionGabriella Vitali Forconesi0Luca Banfi1Andrea Basso2Chiara Lambruschini3Lisa Moni4Renata Riva5Dipartimento di Chimica e Chimica Industriale, Università di Genova, via Dodecaneso 31, 16146 Genova, ItalyDipartimento di Chimica e Chimica Industriale, Università di Genova, via Dodecaneso 31, 16146 Genova, ItalyDipartimento di Chimica e Chimica Industriale, Università di Genova, via Dodecaneso 31, 16146 Genova, ItalyDipartimento di Chimica e Chimica Industriale, Università di Genova, via Dodecaneso 31, 16146 Genova, ItalyDipartimento di Chimica e Chimica Industriale, Università di Genova, via Dodecaneso 31, 16146 Genova, ItalyDipartimento di Farmacia, Università di Genova, viale Cembrano 4, 16147 Genova, ItalyA chiral bio-based building block, prepared by the lipase-mediated desymmetrization of an erythritol derivative, was further functionalized and then submitted to stereoselective Passerini reactions, allowing the synthesis of a small library of new molecules. Thanks to the presence of different functional groups, further cyclizations were performed providing bicyclic polyoxygenated heterocycles.https://www.mdpi.com/1420-3049/25/14/3227multicomponent reactionsPasserini reactiondiastereoselective reactionslipasedesymmetrizationMichael reaction
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Gabriella Vitali Forconesi Luca Banfi Andrea Basso Chiara Lambruschini Lisa Moni Renata Riva
spellingShingle	Gabriella Vitali Forconesi Luca Banfi Andrea Basso Chiara Lambruschini Lisa Moni Renata Riva Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction Molecules multicomponent reactions Passerini reaction diastereoselective reactions lipase desymmetrization Michael reaction
author_facet	Gabriella Vitali Forconesi Luca Banfi Andrea Basso Chiara Lambruschini Lisa Moni Renata Riva
author_sort	Gabriella Vitali Forconesi
title	Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction
title_short	Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction
title_full	Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction
title_fullStr	Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction
title_full_unstemmed	Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction
title_sort	synthesis of polyoxygenated heterocycles by diastereoselective functionalization of a bio-based chiral aldehyde exploiting the passerini reaction
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2020-07-01
description	A chiral bio-based building block, prepared by the lipase-mediated desymmetrization of an erythritol derivative, was further functionalized and then submitted to stereoselective Passerini reactions, allowing the synthesis of a small library of new molecules. Thanks to the presence of different functional groups, further cyclizations were performed providing bicyclic polyoxygenated heterocycles.
topic	multicomponent reactions Passerini reaction diastereoselective reactions lipase desymmetrization Michael reaction
url	https://www.mdpi.com/1420-3049/25/14/3227
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Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction

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