Acetylide Nucleophiles

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Chapter: Organic Chemistry : Planning Organic Syntheses

While the carbonyl group is a very common starting point for bond disconnections in retrosynthetic analysis, an olefinic or acetylenic unit is also a useful reference point in many instances.


ACETYLIDE NUCLEOPHILES

While the carbonyl group is a very common starting point for bond disconnections in retrosynthetic analysis, an olefinic or acetylenic unit is also a useful reference point in many instances. This is because a terminal acetylene can be used as an effective nucleophile to install the triple bond into molecules and it can be reduced stereospecifically to either the cis or trans olefin. Thus for the cis-olefin target T, the following retrosynthetic analysis leads to an efficient synthetic pathway which uses a nucleophilic displacement by an acetylide anion as a key carbon–carbon bond-forming step.


The synthetic sequence would be



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