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

被引：7
|
作者：
Everson, Jack [1 ]
Kiefel, Milton J. [1 ]
机构：
[1] Griffith Univ, Inst Glyc, Gold Coast Campus, Southport, Qld 4222, Australia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 23期
关键词：
LEGIONAMINIC ACID; ASYMMETRIC-SYNTHESIS; ASPERGILLUS-TERREUS; METABOLIC PRODUCTS; PSEUDAMINIC ACID; BUTYROLACTONE-I; LIPOPOLYSACCHARIDES; DERIVATIVES; KDO;
D O I：
10.1021/acs.joc.9b02015
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：15226 / 15235
页数：10
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