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Keywords = oxetanone

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8 pages, 1001 KB  
Article
Copper-Catalyzed Four-Component A3-Based Cascade Reaction: Facile Synthesis of 3-Oxetanone-Derived Spirocycles
by Rongkang Zhang, Liliang Huang, Aiguo Gu and Huangdi Feng
Chemistry 2025, 7(1), 19; https://doi.org/10.3390/chemistry7010019 - 4 Feb 2025
Viewed by 1766
Abstract
3-Oxetanone-derived spirooxazolidines represent a class of building blocks for accessing diverse saturated heterocycles, but their synthetic methods remain unexplored. Herein, we demonstrate a highly atom-economic approach for the synthesis of diverse 3-oxetanone-derived N-propargyl spirooxazolidines via a CuBr2/TFA co-catalyzed four-component A [...] Read more.
3-Oxetanone-derived spirooxazolidines represent a class of building blocks for accessing diverse saturated heterocycles, but their synthetic methods remain unexplored. Herein, we demonstrate a highly atom-economic approach for the synthesis of diverse 3-oxetanone-derived N-propargyl spirooxazolidines via a CuBr2/TFA co-catalyzed four-component A3-based cascade reaction of a 1,2-amino alcohol, a 3-oxetanone, a formaldehyde, and an alkyne. This strategy is characterized by a wide substrate range and excellent chemoselectivity. In addition, the synthesized spirocycles could also be easily converted into other valuable compounds, facilitating potentially useful synthetic applications. Full article
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30 pages, 544 KB  
Article
Cooperative Al(Salen)-Pyridinium Catalysts for the Asymmetric Synthesis of trans-Configured β-Lactones by [2+2]-Cyclocondensation of Acylbromides and Aldehydes: Investigation of Pyridinium Substituent Effects
by Patrick Meier, Florian Broghammer, Katja Latendorf, Guntram Rauhut and René Peters
Molecules 2012, 17(6), 7121-7150; https://doi.org/10.3390/molecules17067121 - 12 Jun 2012
Cited by 49 | Viewed by 8314
Abstract
The trans-selective catalytic asymmetric formation of β-lactones constitutes an attractive surrogate for anti-aldol additions. Recently, we have reported the first catalyst which is capable of forming trans-β-lactones with high enantioselectivity from aliphatic (and aromatic) aldehyde substrates by cyclocondensation with acyl [...] Read more.
The trans-selective catalytic asymmetric formation of β-lactones constitutes an attractive surrogate for anti-aldol additions. Recently, we have reported the first catalyst which is capable of forming trans-β-lactones with high enantioselectivity from aliphatic (and aromatic) aldehyde substrates by cyclocondensation with acyl bromides. In that previous study the concepts of Lewis acid and organic aprotic ion pair catalysis were combined in a salen-type catalyst molecule. Since a pyridinium residue on the salen periphery is essential for high trans- and enantioselectivity, we were interested in the question of whether substituents on the pyridinium rings could be used to further improve the catalyst efficiency, as they might have a significant impact on the effective charges within the heterocycles. In the present study we have thus compared a small library of aluminum salen/bispyridinium catalysts mainly differing in the substituents on the pyridinium residues. As one result of these studies a new catalyst was identified which offers slightly superior stereoselectivity as compared to the previously reported best catalyst. NBO calculations have revealed that the higher stereoselectivity can arguably not be explained by the variation of the effective charge. Full article
(This article belongs to the Special Issue Asymmetric Catalysis)
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8 pages, 82 KB  
Article
Tricarbonyl(h6-Arene)Chromium(0) Complexes as Chiral Auxiliaries: Asymmetric Synthesis of b-Lactones
by Paola Del Buttero and Deborah Montrasio
Molecules 2001, 6(1), 13-20; https://doi.org/10.3390/60100013 - 16 Jan 2001
Cited by 3 | Viewed by 7443
Abstract
The optically pure tricarbonyl(h6-2-substituted benzaldehydes)chromium are used as chiral auxiliaries in the condensation with a series of doubly lithiated carboxylic acids. The intramolecular ring closure of the obtained Cr(CO)3 complexed b-hydroxyacids affords the optically pure b-lactones in satisfactory yield. Full article
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