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Synfacts 2009(2): 0182-0182  
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

Contributor(s): Mark Lautens, Frédéric Ménard
T. E. Reynolds, M. S. Binkley, K. A. Scheidt*
Northwestern University, Evanston, USA
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Publication History

Publication Date:
22 January 2009 (online)

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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.