Al-Catalyzed Enantioselective Dialkylzinc Addition to α-Ketoesters

L. C. Wieland; H. Deng; M. L. Snapper; A. H. Hoveyda

doi:10.1055/s-2005-924771

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Synfacts 2006(2): 0144-0144
DOI: 10.1055/s-2005-924771

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Al-Catalyzed Enantioselective Dialkylzinc Addition to α-Ketoesters

Contributor(s): Mark Lautens, Andrew Martins
L. C. Wieland, H. Deng, M. L. Snapper*, A. H. Hoveyda*
Boston College, Chestnut Hill, USA

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Publikationsdatum:
23. Januar 2006 (online)

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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.