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Synfacts 2007(4): 0428-0428  
DOI: 10.1055/s-2007-968348
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Organocatalytic β -Hydroxylation of Enals

Contributor(s): Benjamin List, Subhas Chandra Pan
S. Bertelsen, P. Dinér, R. L. Johansen, K. A. Jørgensen*
Aarhus University, Denmark
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Publication History

Publication Date:
23 March 2007 (online)

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Significance

An organocatalytic asymmetric β-hydroxylation of α, β-unsaturated aldehydes has been developed. Oximes have been identified as suitable nucleophiles for this reaction and proline-derived catalyst 1 is the best catalyst. Due to the instability of the reaction products, they have been reduced in situ with NaBH4. With 10 mol% of catalyst 1, moderate to good yields (60-75%) and high enantioselectivities (er = 94:6 to 98:2) are obtained for different β-alkyl-substituted enals.