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DOI: 10.1055/s-0033-1340405
Iminophosphorane-Catalyzed Enantioselective Ketimine Nitro-Mannich Reaction
Publication History
Publication Date:
13 December 2013 (online)
![](https://www.thieme-connect.de/media/synfacts/201401/i_b118_s1_10-1055_s-0033-1340405.gif)
Significance
Dixon and co-workers report a new class of bifunctional Brønsted base/H-bond donor organocatalyst. The catalyst (bifunctional iminophosphorane, BIMP) can be applied to the ketimine nitro-Mannich reaction, generating β-nitroamines in good to excellent yields and enantioselectivities.
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Comment
The authors developed a new catalyst motif consisting of a triaryliminophosphorane moiety as a Brønsted base and a thiourea moiety as an H-bond donor. The catalyst can be easily synthesized via Staudinger reaction of an organoazide and a triarylphospine. The efficiency of the catalyst was demonstrated by the application to the first catalytic enantioselective addition of nitromethane to ketone-derived imines under metal-free conditions. The reaction can be scaled up to multigrams and gives access to enantiomerically pure quaternary α-amino acids.
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![](https://www.thieme-connect.de/media/synfacts/201401/i_b118_s1_10-1055_s-0033-1340405.gif)