Enantioselective Hydroamination

By: William Sommer, Aldrich ChemFiles 2009, 9.5, 7.

Aldrich ChemFiles 2009, 9.5, 7.

In 2007, Toste and coworkers reported the first gold-catalyzed enantioselective intramolecular hydroamination of allenes.1 Due to the linear geometry of gold complexes placing the chiral ligand far from the chiral center, LaLonde et al. opted to use a chiral dinuclear-phosphine complex. The allene terminus proved to be amenable to substitution. Linear and cyclic alkanes were tolerated yielding the corresponding pyrrolidines in good yields and excellent selectivity (Scheme 3). In a typical reaction, 3 to 5 mol % of catalyst is used in dichloroethane at room temperature. This first example of enantioselective amination highlights the potency of chiral-gold complexes for asymmetric transformations.

Scheme 3.

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  1. LaLonde, R. L. et al. J. Am. Chem. Soc. 2007, 129, 2452.

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