[nj_bartel]

I'm thinking a certain theoretical compound would work well for a synthesis, but I'm unsure what conditions would be necessary for the compound to exist, nor how to synthesize it.

The compound is a quaternary carbon attached to an R group, a hydrogen, a halogen (probably bromine), and an oxygen which is bound to an alkali metal.


Anyone have any ideas?

[Dan]

If I understand you correctly, this would be a tertiay carbon (as it's bonded to one hydrogen). In this case: too unstable, it will decompose to the aldehyde (assuming R is alkyl) and the alkali metal halogen salt. What are you trying to do, perhaps we can suggest an alternative?

[nj_bartel]

Ah, yes, sorry I misspoke - tertiary carbon.

I'm trying to control alter the Baylis-Hilman reaction in a way such that I can control the stereochemistry of the alcohol carbon in the product, and I thought that that compound could possibly replace the aldehyde, and the stereochemistry could be predetermined in that compound before the reaction.

I'm open to ideas, and thanks for the help - knew it would be unstable, but wasn't sure if there would be any possible conditions where it could exist.

Baylis-Hilman reaction -

[azmanam]

chiral auxiliary as R2?  see the zimmerman traxler transition state model for inspiration

[nj_bartel]

Yes.  I'm going to have to look into that model so I can understand it before I can manipulate it - just starting first sem. organic, but have some prior knowledge that I'm going on.

Thanks.