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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

de Koning, C.B., Giles, R.G.F., Green, I.R. and Jahed, N.M. (2003) The synthesis of R-3-alkoxy-1-(1′-hydroxyethyl)-4-methoxy-2-(1″-propenyl)benzenes utilizing Corey–Bakshi–Shibata asymmetric reductions. Tetrahedron, 59 (17). pp. 3175-3182.

Link to Published Version: http://dx.doi.org/10.1016/S0040-4020(03)00328-4
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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%.

Publication Type: Journal Article
Murdoch Affiliation: School of Mathematical and Physical Sciences
Publisher: Elsevier
Copyright: © 2003 Elsevier Science Ltd.
URI: http://researchrepository.murdoch.edu.au/id/eprint/33715
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