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, no 6, 1536-1537 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2007. Vol. 129, no 6, 1536-1537 p.
IdentifiersURN: urn:nbn:se:uu:diva-121905DOI: 10.1021/ja068908yISI: 000244000700032PubMedID: 17284000OAI: oai:DiVA.org:uu-121905DiVA: diva2:306909