Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 50, Pages 20100-20103Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja208867g
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Funding
- Enantioselective Synthesis Grant
- Canadian Society for Chemistry
- AstraZeneca Canada
- Boehringer Ingelheim (Canada) Ltd.
- Merck Frosst Canada
- NSERC
- University of Ottawa
- Canadian Foundation for Innovation
- Ontario Ministry of Research and Innovation
- AstraZeneca
- American Chemical Society
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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.
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