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Synfacts 2006(2): 0144-0144
DOI: 10.1055/s-2005-924771
DOI: 10.1055/s-2005-924771
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Al-Catalyzed Enantioselective Dialkylzinc Addition to α-Ketoesters
L. C. Wieland, H. Deng, M. L. Snapper*, A. H. Hoveyda*
Boston College, Chestnut Hill, USA
Further Information
Publication History
Publication Date:
23 January 2006 (online)
Significance
The synthesis of chiral α-hydroxy stereocenters continues to be a challenging task. Typical α-hydroxylation methods (MoOPH, oxaziridine, etc.) suffer from poor enantioselectivity in acyclic systems. The asymmetric dialkylzinc addition to α-ketoesters presents a useful alternative. Using an α-amino acid-based ligand in the presence of Al(Oi-Pr)3 and an achiral diethylphosphoramidate, a variety of α-ketoesters were alkylated, affording chiral tertiary alcohols in good to excellent enantiomeric excess.