Reconstruction of Carbon Bond Frameworks via Oxapalladacycles Promoted by the Synergistic Effect of Palladium Catalyst and Triethylborane

Pd-catalyzed beta-carbon elimination of 3-hydroxy-4-pent-enoic acid derivatives promoted by triethylborane proceeds to form conjugated dienes via a decarboxylation process. The formed conjugated dienes undergo the Prins reaction with aldehydes in situ to afford conjugated homoallylic alcohols. These...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 53; no. 17; pp. 3110 - 3120
Main Authors Ninokata, Ryo, Korogi, Riho, Nakao, Junya, Fukuda, Tsutomu, Onodera, Gen, Kimura, Masanari
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.09.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVE METHYLENE-COMPOUNDS
COMPLEXES
C-C bond cleavage
ALDEHYDES
triethylborane
REDUCTIVE ELIMINATION
DIENES
ALLYL ALCOHOLS
BIDENTATE LIGANDS
COUPLING REACTION
palladium
beta-carbon elimination
C-ALLYLATION
HOMOALLYLATION
metallacycles
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Summary:Pd-catalyzed beta-carbon elimination of 3-hydroxy-4-pent-enoic acid derivatives promoted by triethylborane proceeds to form conjugated dienes via a decarboxylation process. The formed conjugated dienes undergo the Prins reaction with aldehydes in situ to afford conjugated homoallylic alcohols. These sequential transformations enable the conversion of diastereomeric mixtures of 3-hydroxy-4-pentenoic acids, which are readily prepared from the simple crossed aldol reaction of esters and alpha,beta-unsaturated aldehydes, into 3,5-hexadienyl alcohols with high regio- and stereoselectivities in a single manipulation.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1485-5781