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)

Full Text: HTML

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]

Related Compounds

  • Pinacolone

Related Articles:

A novel carbonyl reductase with anti-Prelog stereospecificity from Acetobacter sp. CCTCC M209061: purification and characterization.

2014-01-01

[PLoS ONE 9(4) , e94543, (2014)]

Isolation and characterization of 4-tert-butylphenol-utilizing Sphingobium fuliginis strains from Phragmites australis rhizosphere sediment.

2010-10-01

[Appl. Environ. Microbiol. 76(20) , 6733-40, (2010)]

Enhancement of hepatic microsomal esterase activity following soman pretreatment in guinea pigs.

1993-12-03

[Biochem. Pharmacol. 46(11) , 2083-92, (1993)]

Direct conversion of arylamines to pinacol boronates: a metal-free borylation process.

2010-03-01

[Angew. Chem. Int. Ed. Engl. 49(10) , 1846-9, (2010)]

Hg(OTf)2-catalyzed vinylogous semi-pinacol rearrangement leading to 1,4-dihydroquinolines.

2012-03-02

[Org. Lett. 14(5) , 1222-5, (2012)]

More Articles...