A recyclable stereoauxiliary aminocatalyzed strategy for one-pot synthesis of indolizine-2-carbaldehydes

2023 | journal article. A publication with affiliation to the University of Göttingen.

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​A recyclable stereoauxiliary aminocatalyzed strategy for one-pot synthesis of indolizine-2-carbaldehydes​
Zeng, K.; Mei, R.; Dechert, S.; Ackermann, L. & Zhang, K.​ (2023) 
Communications Chemistry6(1).​ DOI: https://doi.org/10.1038/s42004-023-00828-2 

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Authors
Zeng, Kui; Mei, Ruhuai; Dechert, Sebastian; Ackermann, Lutz; Zhang, Kai
Abstract
Abstract Indolizine-carbaldehydes with the easily modifiable carbaldehyde group are important synthetic targets as versatile precursors for distinct indolizines. However, the efficient one-pot construction of trisubstituted indolizine-2-carbaldehydes represents a long-standing challenge. Herein, we report an unprecedented recyclable stereoauxiliary aminocatalytic approach via aminosugars derived from biomass, which enable the efficient one-pot synthesis of desired trisubstituted indolizine-2-carbaldehydes via [3+2] annulations of acyl pyridines and α , β -unsaturated aldehyde. Compared to the steric shielding effect from α -anomer, a stereoauxiliary effect favored by β -anomer of D-glucosamine is supported by control experiments. Furthermore, polymeric chitosan containing predominantly β -D-anhydroglucosamine units also shows excellent catalytic performance in aqueous solutions for the conversion of various substrates, large-scale synthesis and catalytic cycling experiments. Thus, our approach advances the existing methodologies by providing a rich library of indolizine-2-aldehydes. In addition, it delivers an efficient protocol for a set of late-stage diversification and targeted modifications of bioactive molecules or drugs, as showcased with 1,2,3-trisubstituted indolizine-2-carbaldehydes.
Issue Date
2023
Journal
Communications Chemistry 
Organization
Fakultät für Forstwissenschaften und Waldökologie ; Burckhardt-Institut ; Abteilung Holztechnologie und Holzwerkstoffe 
eISSN
2399-3669
Language
English
Sponsor
China Scholarship Council https://doi.org/10.13039/501100004543
Deutsche Forschungsgemeinschaft https://doi.org/10.13039/501100001659
Open-Access-Publikationsfonds 2023

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