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

C.B. de Koning; R.G.F. Giles; I.R. Green; N.M. Jahed

doi:10.1016/S0040-4020(03)00328-4

Back

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

Journal article

Peer reviewed

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

C.B. de Koning, R.G.F. Giles, I.R. Green and N.M. Jahed

Tetrahedron, Vol.59(17), pp.3175-3182

2003

DOI: https://doi.org/10.1016/S0040-4020(03)00328-4

Files and links (1)

url

Link to Published Version *Subscription may be requiredView

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%.

Details

Title: The synthesis of R-3-alkoxy-1-(1′-hydroxyethyl)-4-methoxy-2-(1″-propenyl)benzenes utilizing Corey–Bakshi–Shibata asymmetric reductions
Authors/Creators: C.B. de Koning (Author/Creator) - University of the Witwatersrand
R.G.F. Giles (Author/Creator) - Murdoch University
I.R. Green (Author/Creator) - University of the Western Cape
N.M. Jahed (Author/Creator) - University of the Western Cape
Publication Details: Tetrahedron, Vol.59(17), pp.3175-3182
Publisher: Elsevier
Identifiers: 991005542044007891
Copyright: © 2003 Elsevier Science Ltd.
Murdoch Affiliation: School of Mathematical and Physical Sciences
Language: English
Resource Type: Journal article

UN Sustainable Development Goals (SDGs)

This output has contributed to the advancement of the following goals:

Source: InCites

Metrics

62 Record Views

6 Times Cited - Web of Science

InCites Highlights

These are selected metrics from InCites Benchmarking & Analytics tool, related to this output

Collaboration types: Domestic collaboration; International collaboration
Citation topics: 2 Chemistry; 2.1 Synthesis; 2.1.122 Asymmetric Catalysis
Web Of Science research areas: Chemistry, Organic
ESI research areas: Chemistry