Synthesis of Butenolides via a Horner–Wadsworth–Emmons Cascading Dimerization Reaction

The efficient synthesis of a range of structurally related butenolides has been observed while we were exploring the substrate-scope of a Horner–Wadsworth–Emmons (HWE) reaction. While aliphatic aldehydes gave the expected HWE product, aromatic aldehydes furnished butenolides, resulting from the dime...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-12, Vol.84 (23), p.15226-15235
Main Authors: Everson, Jack, Kiefel, Milton J
Format: Article
Language:English
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Summary:The efficient synthesis of a range of structurally related butenolides has been observed while we were exploring the substrate-scope of a Horner–Wadsworth–Emmons (HWE) reaction. While aliphatic aldehydes gave the expected HWE product, aromatic aldehydes furnished butenolides, resulting from the dimerization of the HWE product during desilylation of the initially formed HWE adduct. In addition to isolating butenolides in a high yield, we have also determined precisely when dimerization occurs.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02015