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Synfacts 2013; 9(1): 0054
DOI: 10.1055/s-0032-1317846
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Iron-Catalyzed Asymmetric Transfer Hydrogenation of Ketimines

Contributor(s):
Hisashi Yamamoto
,
Lan Luo
Mikhailine AA, Maishan MI, Morris RH * University of Toronto, Canada
Asymmetric Transfer Hydrogenation of Ketimines Using Well-Defined Iron(II)-Based Precatalysts Containing a PNNP Ligand.

Org. Lett. 2012;
14: 4638-4641
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

iron - transfer hydrogenation - ketimines

Significance

The authors report an iron-catalyzed asymmetric transfer hydrogenation under mild conditions that gives chiral amines with high enantioselectivity (94–99% ee). The system provides a solution to the challenging C=N bond reduction and proceeds with 2-propanol as the reducing agent.


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Comment

Iron(II)–PNNP complexes that catalyze the asymmetric reduction of N-(diphenylphosphinoyl)- and N-(4-tolylsulfonyl)ketimines were developed. The (R,R)-diamine catalyst produces the (S)-amine. (S,S)-3 are found to be the most active and stereoselective catalyst. The reaction outcome is influenced mainly by the sterics around the imine carbon but is insensitive to its electronic character.


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