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

Søren Bertelsen, Peter Dinér, Rasmus Lyng Johansen, and Karl Anker Jørgensen*
Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark
J. Am. Chem. Soc., 2007, 129 (6), pp 1536–1537
DOI: 10.1021/ja068908y
Publication Date (Web): January 20, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, kaj@chem.au.dk

Abstract

Abstract Image

The first catalytic enantioselective β-hydroxylation of α,β-unsaturated aldehydes is presented. Using commercially available (E)-benzaldehyde oxime in the presence of 2-[bis(3,5-bis-trifluoromethyl-phenyl)trimethyl-silanyloxymethyl]pyrrolidine as organocatalyst, the corresponding chiral carbonyl β-oxime ethers are obtained in high yields and with excellent enantioselectivities. These optically active carbonyl and hydroxy β-oxime ethers are highly interesting biological compounds in, e.g., sex pheromone analogues, highly potent antiinflammatory agents, and penicillin and cephalosporin analogues. The chiral carbonyl β-oxime ethers can be reduced to the corresponding 1,3-diols in high yields. Furthermore, the organocatalytic enantioselective β-hydroxylation of α,β-unsaturated aldehydes could be performed on gram scale without loss of enantioselectivity.

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History

  • Published In Issue February 14, 2007
  • Received December 13, 2006

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