Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 6, Pages 1536-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja068908y
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The first catalytic enantioselective beta-hydroxylation of alpha,beta-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 beta-oxime ethers are obtained in high yields and with excellent enantioselectivities. These optically active carbonyl and hydroxy beta-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 beta-oxime ethers can be reduced to the corresponding 1,3-diols in high yields. Furthermore, the organocatalytic enantioselective beta-hydroxylation of alpha,beta-unsaturated aldehydes could be performed on gram scale without loss of enantioselectivity.
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