Intramolecular Hydroamination

References

1. Crawley, S. L.; Funk, R. L. Org. Lett. 2006, 8, 3995.

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An example of the potency of gold catalysis in hydroamination reactions was highlighted in 2006 by Crawley and Funk in the multistep synthesis of communesin B.¹ One of the key steps in the synthesis was the hydroamination of a terminal alkyl with a secondary amine to provide an enamine via a 7-exo-dig ring formation (Scheme 4). Using AuCl(PPh₃) as catalyst with AgOTf in CH₂Cl₂ at 40 °C yielded the desired product in 89% yield.

Scheme 4.

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Aldrich ChemFiles 2009, 9.5, 3.

Materials