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The synthesis of R-3-alkoxy-1-(1′-hydroxyethyl)-4-methoxy-2-(1″-propenyl)benzenes utilizing Corey-Bakshi-Shibata asymmetric reductions |
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| Authors: | Charles B de KoningRobin G.F Giles Ivan R Green Nazeem M Jahed |
| Affiliation: | a Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, P.O. Wits 2050, Johannesburg 2050, South Africa b Department of Chemistry, Murdoch University, Murdoch, WA 6150, Australia c Department of Chemistry, University of the Western Cape, Private Bag X17, Bellville 7530, South Africa |
| Abstract: | 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%. |
| Keywords: | chiral reductions benzylic alcohols |
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