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Pinacol coupling reaction of beta-halo-alpha,beta-unsaturated aldehydes promoted by TiI4

Pinacol coupling reaction of beta-halo-alpha,beta-unsaturated aldehydes promoted by TiI4

Organic Letters 4(23): 4097-4099

ISSN/ISBN: 1523-7060

PMID: 12423095

DOI: 10.1021/ol026842f

The pinacol reaction of beta-halogenated alpha,beta-unsaturated aldehydes was promoted by titanium tetraiodide to give coupling products in good yields with high dl-selectivity. Subsequent reduction with H2/Pd-C gave saturated vic-diols in good yields. Heck coupling reaction enabled the displacement of halogens with vinyl groups without the loss of stereochemical integrities.

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Accession: 011154990

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