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Asymmetric Organocatalytic β-Hydroxylation of α,β-Unsaturated Aldehydes

S°ren Bertelsen, Peter DinÚr, Rasmus Lyng Johansen, and Karl Anker J°rgensen*

*Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark, Email: kajchem.au.dk

S. Bertelsen, P. DinÚr, R. L. Johansen, K. A. J°rgensen, J. Am. Chem. Soc., 2007, 129, 1536-1537.

DOI: 10.1021/ja068908y (free Supporting Information)


Abstract

An organocatalytic β-hydroxylation of α,β-unsaturated aldehydes with commercially available (E)-benzaldehyde oxime gives the corresponding chiral carbonyl β-oxime ethers in high yields and with excellent enantioselectivities. The chiral carbonyl β-oxime ethers can be reduced to the corresponding 1,3-diols in high yields.

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Key Words

Organocatalysis, 1,3-Diols, O-Alkylation


ID: J48-Y2007-0450