Questions tagged [enolate-chemistry]

The tag has no usage guidance.

4 questions with no upvoted or accepted answers
Filter by
Sorted by
Tagged with
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 ...
3
votes
0answers
54 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
122 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 ...
0
votes
0answers
53 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 ...