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Topic: Cyclisation mechanism using lithium bis(trimethylsilyl)amide that can't quite...  (Read 2218 times)

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Offline Berbik83

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Cyclisation mechanism using lithium bis(trimethylsilyl)amide that can't quite...
« on: August 27, 2015, 03:22:46 PM »
So it seemed pretty simple but I can really figure out the role of the lithium bis(trimethylsilyl)amide to give the azetidinone. I know it is a non-nucleophilic base so my first guess was that the Lithium would coordinate with the oxygen of the ester and help the nucleophilic attack of the amine and then mope the proton...
But not entirely sure.

What you guys think?
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Offline Dan

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Re: Cyclisation mechanism using lithium bis(trimethylsilyl)amide that can't quite...
« Reply #1 on: August 27, 2015, 05:02:03 PM »
Quote from: Berbik83 on August 27, 2015, 03:22:46 PM
I know it is a non-nucleophilic base

Is there anything it could deprotonate (it's a pretty strong base)?
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Offline Berbik83

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Re: Cyclisation mechanism using lithium bis(trimethylsilyl)amide that can't quite...
« Reply #2 on: August 28, 2015, 05:47:55 AM »
True... Sometimes I get kind of blind... Thanks
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Offline TheMantis

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Re: Cyclisation mechanism using lithium bis(trimethylsilyl)amide that can't quite...
« Reply #3 on: September 14, 2015, 12:30:12 AM »
I agree with Dan.  Look for a functionality in your molecule that is acidic and write out the mechanism (arrow pushing) for it using the base.
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