July 09, 2020, 05:17:19 PM
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Topic: Does LDA favor primary or secondary enolates and why?  (Read 198 times)

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Offline JoeyBob

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Does LDA favor primary or secondary enolates and why?
« on: April 06, 2020, 09:26:01 PM »
Like which??


Offline OrganicDan96

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Re: Does LDA favor primary or secondary enolates and why?
« Reply #1 on: April 07, 2020, 06:30:14 AM »
you need to show your working fist, what do you know about LDA?

Offline JoeyBob

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Re: Does LDA favor primary or secondary enolates and why?
« Reply #2 on: April 09, 2020, 06:55:33 PM »
It favors less sterically hindered?

Offline kriggy

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Re: Does LDA favor primary or secondary enolates and why?
« Reply #3 on: April 10, 2020, 03:53:54 PM »
Its dependant on reaction conditions.
In general, using LDA and low temperature favors kinetic enolate such as the one you drew. Using smaller base such as NaH and higher temperature favors the thermodynamic enolate. It can also be formed with bases such as triethylamine and a way how to trap the enolate such as silil protecting group or Bu2BCl because in case of using weak base, the enolate is in equilibrium which favors the thermodynamic product

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