Practical synthesis of 2,5-disubstituted 1,3-dioxolane-4-ones and highly diastereoselective cis-2,5-disubstituted 1,3-dioxolane-4-ones from α-hydroxy acids catalyzed by N-triflylphosphoramide

[Display omitted] N-triflylphosphoramide (NTPA) was found to be an efficient Brønsted acid catalyst for the practical synthesis of 2,5-disubstituted 1,3-dioxolane-4-ones. Racemic and optically pure mandelic acid and lactic acid could be protected using several aldehydes in high selectivity and moder...

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Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 41; pp. 5583 - 5586
Main Author Kucuk, Hatice Baspinar
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 07.10.2015
Elsevier
Subjects
2,5-Disubstituted 1,3-dioxolane-4-ones
Acetalization
Brønsted acid catalyst
Chemistry
Chemistry, Organic
Cyclocondensation
Lactic acid
Mandelic acid
N-triflylphosphoramide
Physical Sciences
Science & Technology
Brønsted acid catalyst
N-triflylphosphoramide
2,5-Disubstituted 1,3-dioxolane-4-ones
Mandelic acid
Acetalization
Cyclocondensation
Lactic acid
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
ONE-POT SYNTHESIS
HETEROSUBSTITUTED CARBOXYLIC-ACIDS
ENOLATE
MANDELIC-ACID
Bronsted acid catalyst
MICHAEL ADDITION
ALCOHOLS
DERIVATIVES
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Summary:[Display omitted] N-triflylphosphoramide (NTPA) was found to be an efficient Brønsted acid catalyst for the practical synthesis of 2,5-disubstituted 1,3-dioxolane-4-ones. Racemic and optically pure mandelic acid and lactic acid could be protected using several aldehydes in high selectivity and moderate yield in the presence of NTPA without azeotropic distillation or use of a dehydrating reagent.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.08.046