Synfacts 2009(1): 0069-0069  
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

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
A. S. Gonzalez, R. G. Arrayas, M. R. Rivero, J. C. Carretero*
Universidad Autonoma de Madrid, Spain
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Publikationsverlauf

Publikationsdatum:
18. Dezember 2008 (online)

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.