Reaction

Ring-Opening of epoxides and aziridines. Asymmetric conjugate addition of organozinc reagents to α,β-unsaturated ketones. Electrophilic addition of olefins. Asymmetric aziridination of olefins. Asymmetric cycloadditions and aldol condensations. Asymmetric Kharasch oxidation. Asymmetric Michael addition of enamides. Asymmetric O-H or O-R insertion reactions. Enantioselective intramolecular aminooxygenation of alkenes. Enantioselective addition of dialkylzinc reagents to N-acylpyridinium salts. Pd-catalyzed C-H functionalizations of oximes with arylboronic acids. Used as a Lewis acid in the Nazarov cyclization. Catalyst in the diacetoxylation olefins. Catalyst in the meta-selective direct arylation of α-aryl carbonyl compounds. Catalyst in the three-component coupling of amines, aldehydes, and alkynes.

Purification Methods

Dissolve it in MeCN, add dry Et2O until cloudy and cool at -20o in a freezer. The light blue precipitate is collected and dried in a vacuum oven at 130o/20mm for 8hours. It has 737nm ( 22.4 max M1cm -1) in AcOH. [Salomon & Kochi J Am Chem Soc 95 330 1973]. It has also been dried in a vessel at 0.1Torr by heating with a Fischer burner [Andrist et al. J Org Chem 43 3422 1978]. It has been dried at 110-120o/5mm for 1hour before use and forms a *benzene complex which should be handled in a dry box because it is air sensitive [Kobayashi et al. Chem Pharm Bull Jpn 28 262 1980, Salomon & Kochi J Am Chem Soc 95 330 1973]. [Beilstein 3 IV 34.]