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Synfacts 2009(1): 0069-0069
DOI: 10.1055/s-0028-1087430
DOI: 10.1055/s-0028-1087430
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Vinylogous Mannich Reaction of Sulfonylimines
A. S. Gonzalez, R. G. Arrayas, M. R. Rivero, J. C. Carretero*
Universidad Autonoma de Madrid, Spain
Further Information
Publication History
Publication Date:
18 December 2008 (online)
![](https://www.thieme-connect.de/media/synfacts/200901/lookinside/thumbnails/10.1055-s-0028-1087430-1.jpg)
Significance
In prior work the authors have reported that catalyst 1 is effective for both Mannich and formal aza Diels-Alder reactions of N-sulfonylimines (J. Am. Chem. Soc. 2004, 126, 456). In the present paper, the utilization of N-(2-thienyl)sulfonyl imines provides vinylogous Mannich products of acyclic silyl dienol ethers and 2-trimethylsilyloxyfuran in high yields and ee values with nearly complete γ-selectivity. Furthermore, the authors demonstrate that the 2-(thienyl)sulfonyl group undergoes facile deprotection by treatment with Mg in MeOH.