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Issue 20, 2004
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Highly stereoselective oxy-Michael additions to α,β-disubstituted nitro olefins: asymmetric synthesis of pseudo-norephedrine derivatives and THP* protected α-hydroxy ketones

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Abstract

The “naked” anion of (S)-6-methyl delta lactol undergoes efficient oxy-Michael addition to α,β-disubstituted nitro olefins to give the THP* protected Henry products with excellent (95→98% de) stereocontrol at the β-position and moderate (up to 3 : 1) stereocontrol at the α-position in favour of the syn-diastereoisomer. Nitro group reduction with in situN-Boc protection and THP* removal provides α,β-disubstituted ethanolamine derivatives, while treatment with tetrapropylammonium perruthenate gives THP* protected α-hydroxy ketone derivatives in high diasteromeric excess.

Graphical abstract: Highly stereoselective oxy-Michael additions to α,β-disubstituted nitro olefins: asymmetric synthesis of pseudo-norephedrine derivatives and THP* protected α-hydroxy ketones

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Publication details

The article was received on 05 May 2004, accepted on 30 Jul 2004 and first published on 22 Sep 2004


Article type: Paper
DOI: 10.1039/B406804C
Citation: Org. Biomol. Chem., 2004,2, 2932-2934
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    Highly stereoselective oxy-Michael additions to α,β-disubstituted nitro olefins: asymmetric synthesis of pseudo-norephedrine derivatives and THP* protected α-hydroxy ketones

    D. J. Buchanan, D. J. Dixon and F. A. Hernandez-Juan, Org. Biomol. Chem., 2004, 2, 2932
    DOI: 10.1039/B406804C

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