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J Am Chem Soc. 2011 Dec 21;133(50):20100-3. doi: 10.1021/ja208867g. Epub 2011 Nov 23.

A catalytic tethering strategy: simple aldehydes catalyze intermolecular alkene hydroaminations.

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  • 1Center for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.

Abstract

Herein we describe a catalytic tethering strategy in which simple aldehyde precatalysts enable, through temporary intramolecularity, room-temperature intermolecular hydroamination reactivity and the synthesis of vicinal diamines. The catalyst allows the formation of a mixed aminal from an allylic amine and a hydroxylamine, resulting in a facile intramolecular hydroamination event. The promising enantioselectivities obtained with a chiral aldehyde also highlight the potential of this catalytic tethering approach in asymmetric catalysis and demonstrate that efficient enantioinduction relying only on temporary intramolecularity is possible.

© 2011 American Chemical Society

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