Synthesis of Butenolides via a Horner-Wadsworth-Emmons Cascading Dimerization Reaction
Abstract
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.
Journal Title
Journal of Organic Chemistry
Volume
84
Issue
23
Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright 2019 American Chemical Society, after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.9b02015
Subject
Medicinal and Biomolecular Chemistry
Organic Chemistry
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
LEGIONAMINIC ACID