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Synlett 2008(7): 995-998  
DOI: 10.1055/s-2008-1072505
LETTER
© Georg Thieme Verlag Stuttgart · New York

Phosphoric Acid Diesters as Efficient Catalysts for Hydroaminations of Nonactivated Alkenes and an Application to Asymmetric Hydroaminations

Lutz Ackermann*, Andreas Althammer
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, 37077 Göttingen, Germany
Fax: +49(551)396777; e-Mail: Lutz.Ackermann@chemie.uni-goettingen.de;
Further Information

Publication History

Received 24 December 2007
Publication Date:
17 March 2008 (online)

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Abstract

Catalytic amounts of phosphoric acid diesters enabled highly efficient intramolecular hydroaminations of nonactivated alkenes. With an enantiomerically enriched Brønsted acid catalyst an unprecedented metal-free asymmetric hydroamination of a nonactivated alkene was accomplished.

Key words

alkenes - amines - asymmetric catalysis - Brønsted acids - phosphates

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15

Acetone, benzene, MTBE, cyclohexane, and CCl4 gave only traces of the desired product.

17

Under these reaction conditions, there was no indication for catalyst decomposition, and primary aminoalkenes reacted less efficiently.

18

Enantiomerically enriched catalyst 3a provided, under otherwise identical reaction conditions, only racemic product.