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Questions tagged [enolate-chemistry]

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2
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1answer
71 views

Can R-3-methyl-4-heptanone be enantioselectively synthesised from 4-heptanone?

I wonder if it is possible to do the following reaction with its enantioselectivity: I am trying to do it via enolate, but I don't know how to make only the R product or if it's even possible to ...
4
votes
1answer
74 views

Role of NaI in Formation of Silyl Enol Ethers using Chloro(trimethyl)silane

I am forming silyl enol ethers using Chloro(trimethyl)silane (TMSCl), and below is an experimental protocol I am following Silyl Enol Ether Synthesis In an oven-dried 100 mL three-necked ...
3
votes
1answer
89 views

Enolate ion opening an epoxide?

Does anyone know if it is possible to open an epoxide and do a 2-C extension using an enolate ion, say, of acetone? Here's an example of what I mean: Based on what I know of enolate chemistry, this ...
0
votes
0answers
61 views

Alkylation of acetophenone

When the NaOH deprotonates the hydrogen off the carbon, I thought there would be a resonance structure, with the negative charge being on both the oxygen and carbon. Since the oxygen is more stable ...
-2
votes
2answers
349 views

Less substituted vs more substituted alkene [closed]

In general, more substituted alkenes are more thermodynamically stable. However, in certain cases such as enamine alkylation, the less substituted double bond is favored. How do we know that which is ...
3
votes
1answer
155 views

How does base size affect the ratio of kinetic/thermodynamic enolate?

One of the factors that favor kinetic products is bulky bases. So, I'd expect that, for a certain substrate, the use of a more bulky base to favor even more the kinetic product. However, in the table ...
3
votes
0answers
59 views

Claisen-like condensation with acid chloride

In the Claisen condensation, an ester enolate attacks an ester, with an alkoxide anion leaving subsequently to give a $\beta$-keto ester. Is it possible for a typical enolate of an aldehyde or ketone ...
2
votes
0answers
127 views

Does the amine used to generate the enolate affect the selectivity of an Evans aldol reaction?

In an Evans aldol reaction, the enolate is typically generated by addition of a boron Lewis acid (e.g. $\ce{(n-Bu)2BOTf}$) and an amine, which acts as a weak base. I'd like to know whether there's any ...
5
votes
0answers
48 views

Increasing C-alkoxycarbonylation of enolates

I am working with N-tosyl-2-piperidone and attempts to use the lithium enolate of this compound to perform an nucleophilic acyl substitution reaction on an several chloroformate esters in THF has lead ...