Synfacts 2009(5): 0509-0509  
DOI: 10.1055/s-0029-1216629
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Induced Vinylogous Mukaiyama Aldol Reaction of Pyruvates

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
M. Frings, I. Atodiresei, J. Runsink, G. Raabe, C. Bolm*
RWTH Aachen, Germany
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Publikationsverlauf

Publikationsdatum:
22. April 2009 (online)

Significance

Extending the scope of their C 1-symmetric amino sulfoximine/copper system, the authors report a highly enantio- and diastereoselective vinylogous Mukaiyama aldol (VMAR) ­reaction of O-silylated dienolates and pyruvates. This catalyst tolerates a wide range of structurally and electronically diverse pyruvate electrophiles to afford products containing two adjacent stereocenters in excellent yields and selectivities.