Class of organosilicon compounds of the form R3Si–O–CR=CR2
The general structure of a silyl enol ether
In organosilicon chemistry, silyl enol ethers are a class of organic compounds that share the common functional group R3Si−O−CR=CR2, composed of an enolate (R3C−O−R) bonded to a silane (SiR4) through its oxygen end and an ethene group (R2C=CR2) as its carbon end. They are important intermediates in organic synthesis.[1][2]
^Peter Brownbridge (1983). "Silyl Enol Ethers in Synthesis - Part I". Synthesis. 1983: 1–28. doi:10.1055/s-1983-30204.
^Ian Fleming (2007). "A Primer on Organosilicon Chemistry". Ciba Foundation Symposium 121 - Silicon Biochemistry. Novartis Foundation Symposia. Vol. 121. Wiley. pp. 112–122. doi:10.1002/9780470513323.ch7. ISBN 978-0-470-51332-3. PMID 3743226.
In organosilicon chemistry, silylenolethers are a class of organic compounds that share the common functional group R3Si−O−CR=CR2, composed of an enolate...
used to install silyl groups onto hindered positions. Silyl triflate is more reactive and also converts ketones to silylenolethers. Silyl triflates are...
generation of the enol often is accompanied by "trapping" or masking of the hydroxy group as an ether, such as a silylenolether. Keto–enol tautomerism refers...
enolether is an alkene with an alkoxy substituent. The general structure is R2C=CR-OR where R = H, alkyl or aryl. A common subfamily of enolethers are...
Ge, Sn, Pb). Such compounds are considered ethers as well. Examples of such ethers are silylenolethers R3Si−O−CR=CR2 (containing the Si−O−C linkage)...
addition is an organic reaction and a type of aldol reaction between a silylenolether (R2C=CR−O−Si(CH3)3) and an aldehyde (R−CH=O) or formate (R−O−CH=O)...
Rubottom oxidation is a useful, high-yielding chemical reaction between silylenolethers and peroxyacids to give the corresponding α-hydroxy carbonyl product...
silylation is to trap silylenolethers, which represent a reactive tautomer of many carbonyl compounds. The introduction of a silyl group(s) gives derivatives...
materials are acetaldehyde and benzophenone which are both converted to silylenolether by reaction with tris(trimethylsilyl)silane and triflic acid with evolution...
is in reaction with silyl chlorides, bromides, and iodides, where the oxygen acts as the nucleophile to produce silylenolether. IUPAC nomenclature Regioisomer...
Like the aldol addition, the Michael reaction may proceed via an enol, silylenolether in the Mukaiyama–Michael addition, or more usually, enolate nucleophile...
(CH3)3SiO3SCF3 is for the preparation of silylenolethers. One example involves the synthesis of the silylenolether of camphor: It was also used in Takahashi...
uses other, similar functional groups as ersatz enols. In the Mukaiyama aldol reaction, silylenolethers add to carbonyls in the presence of a Lewis acid...
perform a Wittig reaction on acylsilane results in the formation of a silylenolether instead of the expected alkene, due to elimination by the carbanion...
the Mukaiyama aldol addition reaction between benzaldehyde and the silylenolether of cyclohexanone with an 81% chemical yield. The corresponding reaction...
nucleophilic compounds like silylenolethers to be used as reagents. A Lewis acid must be added to use silylenolethers but not boron enolates because...
first step, a dirhodium catalyst effects diazo decomposition from silylenolether diazo compound to yield a donor/acceptor cyclopropene. The donor/acceptor...
steps before elimination is carried out. (11) The combination of silylenolethers with palladium(II) acetate (Pd(OAc)2), the Saegusa oxidation, gives...
alkylation. They are also an important intermediate in the formation of silylenolether. Lithium enolate formation can be generalized as an acid–base reaction...
titanium enolates. As a consequence, the double bond geometry in the silylenolether or allylsilane does not translate well into product stereochemistry...
Saegusa, T (1975). "Synthesis of 1,4-diketones by the reaction of silylenolether with silver oxide. Regiospecific formation of silver(I) enolate intermediates"...
Lewis acid and is used to convert carbonyl compounds to acetals and silylenolethers, reacting them together analogously to the aldol reaction. Si–C bonds...
more stable than α-halocarbonyl compounds and are not lachrymators. Silylenolethers undergo many of the same reactions as carbonyl compounds in the presence...
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