Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202300176
Keywords
Bronsted Base; catalysis; conjugate addition; butenolide; quinone
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In this report, the efficient synthesis of interesting molecules through direct 1,6-conjugate addition of butenolide to p-quinone methides via Bronsted base catalysis is presented. The reaction exhibits regioselective gamma-attack of butenolide and demonstrates good functional group tolerance.
Butyrolactones are prevalent structural elements in many natural products. Vinylogous conjugate additions of butenolides are among the most promising synthetic methods for generating natural products and/or natural product-like compounds with potential biological activities. In this report, direct 1,6-conjugate addition of butenolide to p-quinone methides via Bronsted base catalysis was performed, which provides an efficient route to interesting molecules. The reaction proceeds with a regioselective gamma-attack of butenolide and shows good functional group tolerance.
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