Synthesis of Polyoxygenated Heterocycles by Diastereoselective Functionalization of a Bio-Based Chiral Aldehyde Exploiting the Passerini Reaction.
Michael reaction
Passerini reaction
bio-based
biomass
desymmetrization
diastereoselective reactions
lipase
multicomponent reactions
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
15 Jul 2020
15 Jul 2020
Historique:
received:
22
06
2020
revised:
06
07
2020
accepted:
09
07
2020
entrez:
19
7
2020
pubmed:
19
7
2020
medline:
2
3
2021
Statut:
epublish
Résumé
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.
Identifiants
pubmed: 32679733
pii: molecules25143227
doi: 10.3390/molecules25143227
pmc: PMC7397154
pii:
doi:
Substances chimiques
Aldehydes
0
Heterocyclic Compounds
0
Oxides
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Références
Org Lett. 2016 Jul 1;18(13):3306
pubmed: 27276099
J Org Chem. 2014 Jan 3;79(1):339-51
pubmed: 24328226
Beilstein J Org Chem. 2016 Jan 26;12:139-43
pubmed: 26877816
Org Biomol Chem. 2012 Feb 14;10(6):1255-74
pubmed: 22215069
J Org Chem. 2015 Apr 3;80(7):3411-28
pubmed: 25801330
J Org Chem. 2001 Jan 12;66(1):81-8
pubmed: 11429933
Bioorg Med Chem. 1999 Sep;7(9):2095-103
pubmed: 10530960
Molecules. 2016 Aug 30;21(9):
pubmed: 27589709
Mater Sci Eng C Mater Biol Appl. 2017 Sep 1;78:163-174
pubmed: 28575970
ChemSusChem. 2018 May 25;11(10):1621-1627
pubmed: 29624916
Org Lett. 2015 Sep 18;17(18):4636-9
pubmed: 26348005
Nature. 2016 Oct 05;538(7623):27-29
pubmed: 27708325
Org Biomol Chem. 2005 May 7;3(9):1729-37
pubmed: 15858657
Org Lett. 2016 Apr 1;18(7):1638-41
pubmed: 26986694