929029-00-5Relevant academic research and scientific papers
Asymmetric organocatalytic β-hydroxylation of α,β- unsaturated aldehydes
Bertelsen, Soren,Diner, Peter,Johansen, Rasmus Lyng,Jorgensen, Karl Anker
, p. 1536 - 1537 (2007)
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. Copyright
An efficient and enantioselective Michael addition of aromatic oximes to α,β-unsaturated aldehydes promoted by a chiral diamine catalyst derived from α,α-diphenyl prolinol
Chen, Feng,Ren, Hong-Xia,Yang, Yu,Ji, Shan-Ping,Zhang, Zheng-Bing,Tian, Fang,Peng, Lin,Wang, Li-Xin
supporting information, p. 369 - 375 (2017/06/19)
Chiral diamine catalysts 11a–e derived from α,α-diphenyl prolinol were prepared and successfully applied to the Michael addition of aromatic oximes to α,β-unsaturated aldehydes in mediocre to good yields (up to 78%) and good to high enantioselectivities (up to 93% ee).
