As one of the main fragments in medical drugs, spirooxindole has received considerable attention from organic and medicinal chemists. In the past few decades, chemists have been searching for more straightforward and efficient methods to produce compounds containing a spirooxindole fragment. In this regard, isatin-derived Morita-Baylis-Hillman (MBH) carbonates have been widely used as versatile building blocks for the synthesis of spirooxindole structures. This review summarizes the reactions reported in recent years for the construction of the spirooxindole skeleton or C3 disubstituted oxindole derivatives using isatin-derived MBH carbonates and demonstrates the role of isatin-derived MBH carbonates in these reactions.
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http://dx.doi.org/10.1039/d4ob01299b | DOI Listing |
Org Biomol Chem
January 2025
Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P. R. China.
As one of the main fragments in medical drugs, spirooxindole has received considerable attention from organic and medicinal chemists. In the past few decades, chemists have been searching for more straightforward and efficient methods to produce compounds containing a spirooxindole fragment. In this regard, isatin-derived Morita-Baylis-Hillman (MBH) carbonates have been widely used as versatile building blocks for the synthesis of spirooxindole structures.
View Article and Find Full Text PDFChemistry
December 2024
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.
A synergistic Pd/Cu catalyst system has been developed for stereodivergent transformation of Morita-Baylis-Hillman (MBH) carbonates and Schiff bases derived from simple amino acids to afford a series of optically active β-branched γ-methyleneglutamic acid derivatives with adjacent tertiary/tertiary and quaternary/tertiary stereocenters in high yields (up to 96 %) with excellent diastereo- and enantioselectivities (>20/1 dr and >99 % ee in most cases) under mild conditions. The use of SKP ligand is disclosed to be crucial for the success of the transformation, and in particular allowing the reaction to proceed at low catalyst loading (0.02 mol % for Pd and 0.
View Article and Find Full Text PDFOrg Lett
December 2024
Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002, China.
An unexpected phosphine-catalyzed controllable three-component domino reaction involving [1 + 2 + 2] annulation and [1 + 2 + 2]/[3 + 2] sequential annulation reaction of 2-arylmethylidene cyanoacetates/malononitriles with Morita-Baylis-Hillman (MBH) carbonates has been developed. A broad range of densely functionalized cyclopentanes and diquinanes bearing five or four consecutive stereogenic centers, including two all-carbon quaternary stereocenters, were smoothly acquired in moderate to excellent yields under mild reaction conditions from readily available materials. Moreover, this divergent transformation enables the simultaneous generation of three or four new C-C bonds and one or two carbocyclic rings in only one step.
View Article and Find Full Text PDFOrg Lett
October 2024
State Key Laboratory of Southwestern Chinese Medicine Resources, Hospital of Chengdu University of Traditional Chinese Medicine, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P.R. China.
The (3 + 2) cycloaddition of arynes with allylic ylides remains a formidable challenge because both intermediates are highly reactive and prone to spontaneous quenching. Here, we report a (3 + 2) cycloaddition of pyrazolone MBH carbonates with arynes, enabling the efficient synthesis of diverse indene-fused spiropyrazolones. The key is employing a new bifunctional Lewis base catalyst to facilitate the cycloaddition of generated allylic pyridinium ylides with arynes.
View Article and Find Full Text PDFJ Org Chem
November 2024
College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
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