An SPA-triazolium bromide-catalyzed transannular -acylation of enol lactones is presented. This methodology provides convenient access to a range of enantioenriched spirocyclic 1,3-diketones in moderate to high yields and enantioselectivities and features a broad substrate scope in terms of enol lactones. The catalytic capability of this triazolium salt catalyst is also demonstrated in this enantioselective transformation, which could inspire its further application.
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http://dx.doi.org/10.1039/d1cc05205e | DOI Listing |
Org Lett
December 2024
Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati, Assam 781039, India.
Herein, an organocatalytic asymmetric desymmetrizing [4+2] cycloaddition/base-mediated oxidative aromatization reaction sequence has been developed between spirophthalide 2,5-cyclohexadienones and β-methyl cinnamaldehydes. The reaction proceeds through chiral dienamine intermediate formation, and the densely functionalized spirocyclic isobenzofuranone-embedded chiral arenes were formed in high yields with excellent enantioselectivities. A 2-fold desymmetrization reaction was also performed, and the products were obtained in high enantioselectivities.
View Article and Find Full Text PDFAnal Chem
December 2024
Guangdong Key Laboratory of Nanomedicine, CAS-HK Joint Lab of Biomaterials, CAS Key Laboratory of Biomedical Imaging Science and System, Institute of Biomedicine and Biotechnology, Shenzhen Institutes of Advanced Technology (SIAT), Chinese Academy of Sciences, Shenzhen 518055, P. R. China.
Lysosomes are acidic membrane-bound organelles that aid digestion, excretion, and cell renewal. The lysosomal membranes are essential for maintaining lysosomal functions and cellular homeostasis. In this work, we developed a molecular "NOR" logic gate, , by introducing malachite green into the spirocyclic rhodamine.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Xi'an Jiaotong University, Frontier Institute of Science and Technology, 99 Yanxiang road, Yanta district, 710054, Xi'an, CHINA.
Although great advancement has been made in synthesis of 3D bridged bicyclic[n.1.1]-bioisosteres, facile construction of 2D/3D merged molecules incorporating bridged rings, as novel chemical space in drug discovery, remains a significant challenge.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Department of Chemistry, New York University, New York, New York 10003, United States.
Complexity-generating reactions that access three-dimensional products from simple starting materials offer substantial value for drug discovery. While oxygen-containing heterocycles frequently feature unique, nonaromatic architectures such as spirocyclic rings, exploration of these chemical spaces is limited by conventional synthetic approaches. Herein, we report a copper-catalyzed annulation and alkene transposition cascade reaction that enables a modular preparation of complex, spirocyclic ethers from readily available alkenol substrates via a copper-catalyzed annulation and transannular 1,5-hydrogen atom transfer-mediated C-H functionalization.
View Article and Find Full Text PDFOrg Lett
December 2024
State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
A bioinspired alkylation dearomatization reaction was developed to construct the 5/6/6 fused-spiro tricyclic core framework and spiro-quaternary carbon chiral center. The usage of this approach for assembling these natural products of spirocyclic polycyclic polyprenylated acylphloroglucinols with an octahydrospiro-[cyclohexan-1,5'-indene] core is demonstrated by the first asymmetric total synthesis of highly oxidized hyperbeanol A.
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