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Synfacts 2007(4): 0393-0393
DOI: 10.1055/s-2007-968361
DOI: 10.1055/s-2007-968361
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Catalytic Enantioselective Mannich-Type Reactions of Ketoimines
Y. Suto, M. Kanai*, M. Shibasaki*
The University of Tokyo, Japan
Further Information
Publication History
Publication Date:
23 March 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200704/lookinside/thumbnails/10.1055-s-2007-968361-1.jpg)
Significance
The authors describe the enantioselective Mannich-type reaction using silyl ketene acetals and ketoimines as substrates. CuOAc was shown to be the best copper source. Very high ee values were obtained for aryl,alkyl-ketoimines, while slightly lower ee values were obtained for alkyl,alkyl-ketoimines. The use of a DuPHOS derivative proved to be the optimal chiral ligand for alkyl,alkyl-ketoimines, while DTBM-SEGPHOS was best for aryl,alkyl-ketoimines. Use of a silicon-containing additive proved necessary for catalyst turnover. Removal of the N-phosphinoyl group was shown to proceed with 3 N HCl in THF.