Wednesday, November 4, 2009

Somebody Explain

Am I missing something?



This is a really expensive and complicated way to do a sophomore organic reaction. Instead of making the silyl enol ether and treating it with stoichiometric CAN and 2,6-di-tBuPy (both expensive and used in large excess 2 eq and 4 eq respectively), why not just deprotonate with LDA and add an allyl halide?

Can anyone think of a reason to do this reaction (aside from somehow publishing it in Org Lett)?

5 comments:

scientist 1 said...

It does seem a little silly. I didn't search to see if any of the substrates were unusual in their reactivity, but a general substructure search showed that base and allyl halide seems to work very well.

Anything to get funding, apparently.

Mike said...

silicon tethers! the solution to, and cause of all of life's problems...

Jim said...

Did you cleavage the tether?

scientist 1 said...

I feel that he cleavaged it.

Mike said...

yes...i just cleavaged some yesterday. i also added one small particle of DMAP to my acylation.