76436-98-1Relevant academic research and scientific papers
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.
Anti aldol selectivity in a synthetic approach to the C1-C 12 fragment of the tedanolides
Jung, Michael E.,Zhang, Ting-Hu
, p. 137 - 140 (2008/09/17)
In a synthetic approach to the completely protected C1 C 12 fragment of the macrocyclic cytotoxic agent tedanolide 1, we carried out the tin-catalyzed Mukaiyama aldol reaction between the 2,3-dialkoxypropanal 5 and the silyl enol eth
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
A stereoselective isomerization of allyl silyl ethers to (E)- Or (Z)-silyl enol ethers using cationic iridium complexes
Ohmura, Toshimichi,Shirai, Yasuo,Yamamoto, Yasunori,Miyaura, Norio
, p. 1337 - 1338 (2007/10/03)
A cationic indium complex, prepared via the hydrogenation of [Ir(cod)2]PF6-2PPr3 is found to be an excellent catalyst for the stereoselective isomerization of primary allyl silyl ethers to (E)-enol ethers and secondary all
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.
SYNTHETIC ORGANIC REACTIONS BY MEANS OF REACTIVE NUCLEOPHILES GENERATED THROUGH REARRANGEMENT OF SILYL GROUP
Kuwajia, Isao
, p. 137 - 148 (2007/10/02)
Under basic conditions, 1-(trialkylsilyl)-allylic and -propargylic alcohols have been shown to undergo 1,2-rearrangement of a silyl group from carbon to oxygeen to generate the corresponding 3-siloxyallyl and allenyl anionic species.Their synthetic utilit
BASE-INDUCED REARRANGEMENT OF 1-(TRIMETHYLSILYL)ALLYLIC ALCOHOLS. STEREO- AND REGIOSELECTIVE SYNTHESIS OF SILYL ENOL ETHERS THROUGH LITHIUM HOMOENOLATES.
Kato,Mori,Oshino,Enda,Kobayashi,Kuwajima
, p. 1773 - 1778 (2007/10/02)
1-(Trimethylsilyl)allylic alcohols have been prepared and their conversions to silyl enol ethers have been examined. Under appropriate conditions, lithium alkoxides of the above alcohols are in equilibrium with lithium homoenolates, 3-(trimethylsiloxy)allyllithiums, which react with alkyl iodides to give the silyl enol ethers of defined stereo- and regiochemistry. Further, a catalytic amount of butyllithium induces the rearrangement of the alcohols to yield the corresponding silyl enol ethers in a highly stereo- and regiocontrolled manner via self-protolysis. Equilibrium composition between lithium alkoxides and lithium homoenolates has been shown to be greatly influenced by the steric factors around alpha carbons of allylic alcohols.
A REGIOSPECIFIC SYNTHESIS OF TRIMETHYLSILYL ENOL ETHERS USING RHODIUM CATALYZED ISOMERIZATION OF β-TRIMETHYLSILYLALLYL ALCOHOLS
Matsuda, Isamu,Sato, Susumu,Izumi, Yusuke
, p. 2787 - 2790 (2007/10/02)
The rhodium catalyzed isomerization of β-trimethylsilylallyl alcohols has been successfully applied for the regiospecific synthesis of trimethylsilyl enol ethers.
STEREO- AND REGIO-SELECTIVE CONVERSION OF 1-TRIMETHYLSILYLALLYLIC ALCOHOLS INTO THE SILYL ENOL ETHERS CATALYZED BY BUTHYLLITHIUM
Kuwajima, Isao,Kato, Masahiro,Mori, Akio
, p. 2745 - 2748 (2007/10/02)
(Z)-Silyl enol ethers can be prepared selectively with complete regio-specificity by treating 1-trimethylsilylallylic alcohols with a catalytic amount of buthyllithium.
