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Synfacts 2009(2): 0182-0182
DOI: 10.1055/s-0028-1087645
DOI: 10.1055/s-0028-1087645
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Addition to Sulfinylimines via Brook Rearrangement of Hydroxypropargylsilanes
T. E. Reynolds, M. S. Binkley, K. A. Scheidt*
Northwestern University, Evanston, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. Januar 2009 (online)
![](https://www.thieme-connect.de/media/synfacts/200902/lookinside/thumbnails/10.1055-s-0028-1087645-1.jpg)
Significance
A wide range of β-ketoamine derivatives 3 can be prepared with high levels of selectivity for both the amine and the alkene found in 3. The products obtained correspond to that resulting from an aza-Morita-Baylis-Hillman reaction. However, the advantage of the new procedure is that the geometry of the alkene is fully controlled, whereas the aza-MBH reaction typically leads to E/Z mixtures when R¹ and R³ are similar in steric bulk.