Organic Letters 2002-11-14

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

Makoto Shimizu, Hiroshi Goto, Ryuuichirou Hayakawa

Index: Org. Lett. 4(23) , 4097-9, (2002)

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Abstract

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 H(2)/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. [reaction: see text]