Categories: C-C Bond Formation > Oxygen-containing molecules > α,β-unsaturated compounds >
Synthesis of enones
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Recent Literature
Highly regioselective vinylation of electron-rich olefins by halostyrenes is
effected by palladium catalysis with either mono- or bidentate phosphines in
DMSO as solvent. The use of hemilabile 1,3-bis(diphenylphosphino)propane
monoxide as a ligand led to faster reactions of more challenging 2-substituted
vinyl ethers and reduced Pd loadings.
M. McConville, O. Saidi, J. Blacker, J. Xiao, J. Org. Chem., 2009,
74, 2692-2698.
1-Siloxy-1-alkenylcopper species were generated by 1,2-Csp2-to-O
silyl migration of the copper enolates of acyltriphenylsilanes. The
alkenylcopper species reacted with methyl, benzyl, allylic, tributylstannyl
halides and in the presence of Pd(0) catalyst with aryl and alkenyl iodides
to give geometrically pure (Z)-enol silyl ethers.
A. Tsubouchi, K. Onishi, T. Takeda, J. Am. Chem. Soc., 2006,
128, 14268-14269.
A 1,4-dipolar intermediate generated from pyridine and dimethyl
acetylenedicarboxylate reacted with aldehydes to give 2-benzoylfumarates via
the elimination of pyridine, whereas with N-tosylimines as
dipolarophiles the reaction afforded highly substituted 1-azadienes.
V. Nair, A. R. Sreekanth, N. Abhilash, A. T. Biju, B. R. Devi, R. S. Menon,
N. P. Rath, R. Srinivas, Synthesis,
2003, 1895-1902.
The Rh(I)-catalyzed [3 + 2] cycloaddition of cyclopropenones and alkynes
provides a highly efficient and regioselective route to cyclopentadienones (CPDs)
that would be otherwise difficult to obtain. The versatility of the method
is explored with a wide range of alkynes and diaryl- as well as
arylalkylcyclopropenones.
P. A. Wender, T. J. Paxton, T. J. Williams, J. Am. Chem. Soc., 2006,
128, 14814-14815.
