ORGLIST: Conjugate Reduction and Side Reactions

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From: Jeremy M. Carr (carr030$##$
Date: Thu Oct 25 2007 - 10:59:36 EDT

I'm currently trying to do a conjugate reduction on methyl (E)-5-
phenyl-2-pentenoate to give the corresponding aliphatic ester. There
are numerous examples of this in the literature, but they either
feature enantioselective methods (using a chiral ligand) or
ridiculously air-sensitive compounds (Stryker's reagent). I found a
recent reference suggesting that Phebox Rh(I) and triethoxysilane in
60 C toluene will do the desired transformation in an hour. I've
substituted Wilkinson's catalyst and got a mixture of products;
eventually, I found the desired product, but it looks like roughly
50% conversion.

Has anyone had success doing a similar reaction? Will Wilkinson's
contribute to side reactions?

Does anyone know about reacting the generated silyl enol ether with a
bromonium source to trap the corresponding alpha-bromide?


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