Categories: O-Si Bond Formation >
Synthesis of silyl enol ethers and related compounds
Recent Literature
Various ionic liquids have been tested for the
preparation of silyl enol ethers from aldehydes and ketones with
(bistrimethylsilyl)acetamide (BSA). Yields have been strongly influenced by the
nature of the cation of the ionic liquid.
M. Smietana, C. Mioskowski, Org. Lett., 2001, 3,
1037-1039.
N,O-Silyl dienyl ketene acetals are useful reagents for highly
enantioselective vinylogous aldol additions to various aldehydes in the presence of SiCl4 and the catalytic action of
a chiral
phosphoramide.
S. E. Denmark, J. R. Heemstra, Jr., J. Am. Chem. Soc.,
2006, 128, 1038-1039.
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.
