α-Hydroxylation of carbonyls using iodine

[Display omitted] The α-hydroxylation of ketones and aldehydes to α-hydroxyketals mediated by iodine under basic conditions in MeOH is described. Enolates generated under the reaction conditions are iodinated and the resulting α-iodocarbonyl is transformed into the hydroxyketal. The use of iodine fo...

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Bibliographic Details
Published inTetrahedron letters Vol. 46; no. 3; pp. 447 - 450
Main Authors Zacuto, Michael J., Cai, Dongwei
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.01.2005
Elsevier
Subjects
Acyloins
Chemistry
Chemistry, Organic
Iodine
Physical Sciences
Science & Technology
α-Hydroxylation
α-Hydroxylation
Acyloins
Iodine
ORGANIC-SYNTHESIS
KETONES
ROUTE
ETHERS
INDIRECT ELECTROCHEMICAL OXIDATION
HYPERVALENT IODINE
alpha-hydroxylation
RING SIZE
iodine
FACILE
AMINOXYLATION
acyloins
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Summary:[Display omitted] The α-hydroxylation of ketones and aldehydes to α-hydroxyketals mediated by iodine under basic conditions in MeOH is described. Enolates generated under the reaction conditions are iodinated and the resulting α-iodocarbonyl is transformed into the hydroxyketal. The use of iodine for this chemistry represents an economical and practical alternative to existing methods for this transformation.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.11.092