The synthesis of R-3-alkoxy-1-(1′-hydroxyethyl)-4-methoxy-2-(1″-propenyl)benzenes utilizing Corey–Bakshi–Shibata asymmetric reductions

Pyrolysis of the 3- O-allyl derivative 7 of isovanillin followed by alkylation of the derived allylphenol 8 afforded a series of benzaldehyde derivatives 9– 11 each of which was transformed by initial treatment with methylmagnesium bromide followed by oxidation of the corresponding alcohols with act...

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Bibliographic Details
Published inTetrahedron Vol. 59; no. 17; pp. 3175 - 3182
Main Authors de Koning, Charles B, Giles, Robin G.F, Green, Ivan R, Jahed, Nazeem M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.04.2003
Elsevier
Subjects
benzylic alcohols
Chemistry
Chemistry, Organic
chiral reductions
Physical Sciences
Science & Technology
chiral reductions
benzylic alcohols
ALCOHOLS
KETONES
CATALYSIS
MECHANISM
CHEMICAL-SHIFTS
ENANTIOSELECTIVE REDUCTION
BORANE REDUCTION
OXAZABOROLIDINES
ENANTIOMER
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Summary:Pyrolysis of the 3- O-allyl derivative 7 of isovanillin followed by alkylation of the derived allylphenol 8 afforded a series of benzaldehyde derivatives 9– 11 each of which was transformed by initial treatment with methylmagnesium bromide followed by oxidation of the corresponding alcohols with activated manganese dioxide into a series of ketones 15– 17 . Palladium(0) catalysed isomerization of the double bond in the prop-2′-enyl side-chain afforded ketones 36– 38 which were subjected to the Corey–Bakshi–Shibata asymmetric reduction protocol to afford the R-3-alkoxy-1-(1′-hydroxyethyl)-4-methoxy-2-(1″-propenyl) benzenes 42– 44 in yields of approximately 60% and with ee's of 75%. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)00328-4