Highly effective vinylogous Mukaiyama-Michael reaction catalyzed by silyl methide species generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane.
Silyl methide species in situ generated from 1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane (Tf(2)CHCH(2)CHTf(2)) performed as an excellent acid catalyst for the vinylogous Mukaiyama-Michael reaction of alpha,beta-unsaturated ketones with 2-silyloxyfurans. Notably, the required loading of Tf(2)CHCH(2)CHTf(2) to obtain the 1,4-adducts in reasonable yield was significantly low (from 0.05 to 1.0 mol %). This carbon acid-mediated VMM reaction provides a powerful synthetic methodology to construct highly substituted gamma-butenolide structure.
Takahashi
Arata
A
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Yanai
Hikaru
H
Zhang
Min
M
Sonoda
Takaaki
T
Mishima
Masaaki
M
Taguchi
Takeo
T
D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D011407:Propane / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
C549277:1,1,3,3-tetrakis(trifluoromethanesulfonyl)propane; D005663:Furans; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D017646:Organosilicon Compounds; D011407:Propane