76436-98-1Relevant articles and documents
REGIO- AND STEREODEFINED SYNTHESIS OF TRIMETHYLSILYL ENOL ETHERS RESULTED FROM THE ISOMERIZATION OF α-TRIMETHYLSILYL KETONES
Matsuda, Isamu,Sato, Susumu,Hattori, Motoaki,Izumi, Yusuke
, p. 3215 - 3218 (1985)
The isomerization of an α-trimethylsilyl ketone is lead to the corresponding trimethylsilyl enol ether with the enhanced regioselectivity by heating or by the assist of trimethylsilyl trifluoromethanesulfonate.The thermal reaction discloses a new regiodefined (E)-selective route to silyl enol ethers.
A new method for the preparation of silyl enol ethers from carbonyl compounds and (trimenthylsily)diazomethane in a regiospecific and highly stereoselective manner
Aggarwal, Varinder K.,Sheldon, Chris G.,Macdonald, Gregor J.,Martin, William P.
, p. 10300 - 10301 (2007/10/03)
The reaction of lithium (trimethylsilyl)diazomethane with aldehydes and ketones has been investigated, and it has been found that quenching at low temperature with MeOH followed by addition of Rh2(OAc)4 gave silyl enol ethers in high yields. Quenching with other electrophiles (e.g., deuterium, MeI) gave terminal and substituted silyl enol ethers with complete control over regio- and stereochemistry. The mechanism of this novel process has been mapped out through a combination of deuterium labeling, ReactIR, and isolation of reaction intermediates. Copyright
REGIO- AND STEREOSELECTIVE PREPARATION OF SILYL ENOL ETHERS BY ALKYLIDENATION OF SILYL ESTERS
Takai, Kazuhiko,Kataoka, Yasutaka,Okazoe, Takashi,Utimoto, Kiitiro
, p. 1065 - 1068 (2007/10/02)
Treatment of trimethylsilyl esters with a reagent for alkylidenation of carbonyl groups derived from 1,1-dibromoalkane, zinc, TiCl4, and TMEDA in THF gives Z-trimethylsilyl enol ethers in a regio- and stereoselective manner.
