Intramolecular Hydroamination

By: William Sommer, Aldrich ChemFiles 2009, 9.5, 3.

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

     
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