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Synfacts 2010(10): 1153-1153
DOI: 10.1055/s-0030-1258646
DOI: 10.1055/s-0030-1258646
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Enantioselective Aza-Diels-Alder Reactions
U. K. Tambar, S. K. Lee, J. L. Leighton*
Columbia University, New York, USA
Further Information
Publication History
Publication Date:
22 September 2010 (online)
Significance
The aza-Diels-Alder reaction is an efficient and direct method for preparing useful piperidines (see Review below). Enantioselective variants have mostly been limited to highly reactive Danishefsky-type dienes. The authors present a highly enantioselective (formal) aza-Diels-Alder reaction between glyoxylate- and aliphatic aldehyde-derived hydrazones and non-Danishefsky-type dienes. The reaction utilizes a readily available chiral silane to induce asymmetry.
Review: P. Buonora, J.-C. Olsen, T. Oh Tetrahedron 2001, 57, 6099-6138.