Sc(OTf)3-catalyzed indolylation of 1,2-allenic ketones: controlled highly selective synthesis of beta-indolyl-alpha,beta-unsaturetated (E)-enones and beta,beta-bisindolyl ketones.
[reaction: see text] A novel highly stereoselctive synthesis of beta-indolyl-alpha,beta-unsaturated (E)-enones by the hydroindolylation of the beta,gamma-C=C bond of 1,2-allenic ketones in the presence of 5 mol % Sc(OTf)(3) was developed. beta,beta-Bisindolyl ketones were prepared by using 2.5 equiv of indoles. A stepwise protocol for introducing different indoles was also established.
Ma
Shengming
S
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai. masm@mail.sioc.ac.cn
Yu
Shichao
S
D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
D007211:Indoles; D007659:Ketones; D008698:Mesylates; D009942:Organometallic Compounds; C012077:trifluoromethanesulfonic acid; D012538:Scandium