Volume 2009, Issue 10 p. 1606-1611
Full Paper

Synthesis of Enantioenriched Secondary and Tertiary Alcohols via Tricarbonylchromium(0) Complexes of Benzyl Allyl Ethers

Keren Abecassis

Keren Abecassis

Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, UK, Fax: +44-207-594-5804

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Susan E. Gibson

Susan E. Gibson

Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, UK, Fax: +44-207-594-5804

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Mar Martin-Fontecha

Mar Martin-Fontecha

Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, UK, Fax: +44-207-594-5804

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First published: 13 March 2009
Citations: 9

Graphical Abstract

The tricarbonylchromium(0) complexes of benzyl allyl ethers undergo enantioselective deprotonation/alkylation reactions to giveenantioenriched imidazole alcohols, a triol and a tertiary alcohol after removal of the allyl group.

Abstract

Allyl ethers of the tricarbonylchromium(0) complexes of benzylic alcohols undergo highly enantioselective benzylic functionalisation using a chiral base/electrophilic quench sequence; the allyl group is readily removed to reveal a hydroxy group as demonstrated in the syntheses of enantioenriched imidazole alcohols, a triol and a tertiary alcohol. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)