Morita–Baylis–Hillman Spirannulation under Phosphine- and Anion-Binding Catalysis

We introduce an advancement in Morita–Baylis–Hillman (MBH) chemistry that provides access to α-spirannulated enones. The treatment of enone-tethered azaarenium salts with catalytic amounts of organophosphines provides spiroindenyl dihydropyridines. It represents the α-spirannulation of enones via an...

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Bibliographic Details
Published in:Organic letters 2024-04, Vol.26 (15), p.3273-3278
Main Authors: Singh, Bara, Pandey, Shivam K., Malik, Nirmal, Ramasastry, S. S. V.
Format: Article
Language:English
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Summary:We introduce an advancement in Morita–Baylis–Hillman (MBH) chemistry that provides access to α-spirannulated enones. The treatment of enone-tethered azaarenium salts with catalytic amounts of organophosphines provides spiroindenyl dihydropyridines. It represents the α-spirannulation of enones via an intramolecular MBH (IMBH) reaction utilizing dual phosphine- and anion-binding catalysis. The IMBH adducts were subjected to several post-synthetic modifications to access highly functionalized molecules.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00847