Asymmetric organocatalytic beta-hydroxylation of alpha, beta-unsaturated aldehydes
2007 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 129 1536-1537, no 6, 1536-1537 p.Article in journal (Refereed) PublishedText
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.
Place, publisher, year, edition, pages
American Chemical Society (ACS), 2007. Vol. 129 1536-1537, no 6, 1536-1537 p.
IdentifiersURN: urn:nbn:se:kth:diva-179960DOI: 10.1021/ja068908yOAI: oai:DiVA.org:kth-179960DiVA: diva2:891045
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