Convenient synthesis of O-functionalized mandelic acids via Lewis acid mediated transformation of 1,3-dioxolan-4-ones

An efficient method for the synthesis of O-substituted mandelic acids containing alkenyl, alkynyl, methoxycarbonyl, or phenacyl fragments via the Lewis acid-catalyzed reaction of 1,3-dioxolan-4-ones with different C-nucleophiles is proposed. [Display omitted]

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Bibliographic Details
Published inTetrahedron Vol. 75; no. 26; pp. 3570 - 3578
Main Authors Shcherbinin, Vitaly A., Konshin, Valery V.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.06.2019
Elsevier
Subjects
1,3-Dioxolan-4-one
1-Alkyne
C-nucleophile
Chemistry
Chemistry, Organic
Oxocarbenium cation
Physical Sciences
Science & Technology
1,3-Dioxolan-4-one
C-nucleophile
Oxocarbenium cation
1-Alkyne
ALCOHOLS
INSERTION
POTENT
FACILE SYNTHESIS
ANALOGS
ALDEHYDES
CARBOXYLIC-ACIDS
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Summary:An efficient method for the synthesis of O-substituted mandelic acids containing alkenyl, alkynyl, methoxycarbonyl, or phenacyl fragments via the Lewis acid-catalyzed reaction of 1,3-dioxolan-4-ones with different C-nucleophiles is proposed. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.05.025