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Synfacts 2013; 9(1): 0058
DOI: 10.1055/s-0032-1317779
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Enantioselective Aza-Morita–Baylis–Hillman Reaction

Contributor(s):
Hisashi Yamamoto
,
Susumu Oda
Hyodo K, Nakamura S, * Shibata N. * Nagoya Institute of Technology, Japan
Enantioselective Aza-Morita–Baylis–Hillman Reactions of Acrylonitrile Catalyzed by Palladium(II) Pincer Complexes having C 2-Symmetric Chiral Bis(imidazoline) Ligands.

Angew. Chem. Int. Ed. 2012;
51: 10337-10341
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

palladium - bis(imidazoline) ligands - aza-Morita–Baylis–Hillman reaction

Significance

This paper describes the palladium-catalyzed enantioselective aza-Morita–Baylis–Hillman reaction of acrylonitriles with imines. The bulky pincer ligand enabled the synthesis of enantioenriched α-methylene-β-aminonitriles in high yield.


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Comment

The palladium–pincer complex preferably activates acrylonitrile, even in the presence of ethyl acrylate. The palladium ketenimide is a key intermediate for the asymmetric induction. The palladium complex may promote other Lewis acid catalyzed reactions.


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