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-Heterocyclic carbenes (NHCs) catalyze the silyl transfer from trialkylsilyl ketene acetals to ketones. A series of enolizable ketones as well as cyclohexanecarboxaldehyde were efficiently converted into the corresponding silyl enol ethers at 23°C in THF.
J. J. Song, Z. Tan, J. T. Reeves, D. R. Fandrick, N. K. Yee, C. H. Senanayake, Org. Lett., 2008, 10, 877-880.

An efficient, practical, robust method for the regio- and stereoselective preparation of ketene trimethylsilyl acetals derived from tert-butyl esters can be performed under convenient reaction conditions: LDA-TMSCl, 0-5 °C, and cyclopentyl methyl ether (CPME) as solvent. The stereocontrolled preparation of highly reactive β-ketoester-derived tert-butyl (1Z,3E)-1,3-bis(TMS)dienol ethers is also described.
T. Okabayashi, A. Iida, K. Takai, Y. Nawate, T. Misaki, Y. Tanabe, J. Org. Chem., 2007, 72, 8142-8145.

T. Okabayashi, A. Iida, K. Takai, Y. Nawate, T. Misaki, Y. Tanabe, J. Org. Chem., 2007, 72, 8142-8145.

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-C^sp2-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.