Organocatalysis as a safe practical method for the stereospecific dibromination of unsaturated compounds.

Gloria Hernández-Torres, Bin Tan, Carlos F Barbas

The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 Torrey Pines Road, La Jolla, California 92037, USA.

Organic letters 2012 Apr 6

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Organocatalytic stereospecific dibromination of a wide variety of functionalized alkenes was achieved using a stable, inexpensive halogen source, 1,3-dibromo 5,5-dimethylhydantoin, and a simple thiourea catalyst at room temperature. The presence of a tertiary amine enhanced the rate of the dibromination reaction, and yields were good in various solvents, including aqueous solvents. The procedure was extended to alkynes and aromatic rings and to dichlorination reactions by using the 1,3-dichloro hydantoin derivative.

Citation

Gloria Hernández-Torres, Bin Tan, Carlos F Barbas. Organocatalysis as a safe practical method for the stereospecific dibromination of unsaturated compounds. Organic letters. 2012 Apr 6;14(7):1858-61