Questions tagged [protecting-groups]

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6
votes
1answer
2k views

Can a benzyl ether be removed in the presence of an ester?

I'd like to deprotect a benzyl group for a Fráter–Seebach alkylation. Would it be possible to do this with a Birch reduction using Li/NH3 (or Na/NH3), without also reducing the ester carbonyl group? ...
5
votes
3answers
508 views

Effect of protecting group on diastereoselectivity of LiAlH4 reduction of α-hydroxyketones

In the reactions above, taken from Tetrahedron Lett. 1982, 23 (23), 2355–2358, the choice of protecting group on the α-hydroxyl group has a large influence on the diastereoselectivity of reduction. ...
1
vote
1answer
371 views

Can an ether be selectively hydrolysed in the presence of an ester?

What reaction, or protection/deprotection can be used to transform the ether group of a molecule that also has an ester compound into an alcohol while keeping the ester unchanged? For example: The ...