Synfacts 2011(5): 0519-0519  
DOI: 10.1055/s-0030-1259834
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Iridium and Enamine Catalysis

Contributor(s): Mark Lautens, Jane Panteleev
A. Quintard, A. Alexakis*, C. Mazet*
Université de Genève, Switzerland
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Publikationsverlauf

Publikationsdatum:
15. April 2011 (online)

Significance

A one-pot, two-step iridium-catalyzed isomerization of allylic alcohols 1 and subsequent organocatalytic α-alkylation is described. The iridium-catalyzed isomerization makes this process complementary to the more classical strategy of 1,4-addition followed by enamine (or enolate) alkylation to access these synthons. Using a chiral iridium catalyst and a chiral proline-based catalyst highly complex α,β-chiral aldehydes are obtained with great enantiocontrol. Preliminary investigations on a kinetic resolution are also discussed.